U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C62H111N11O12
Molecular Weight 1202.6112
Optical Activity UNSPECIFIED
Defined Stereocenters 12 / 12
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of CYCLOSPORINE

SMILES

[H][C@@]1([C@H](O)[C@H](C)C\C=C\C)N(C)C(=O)[C@H](C(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)N(C)C(=O)[C@@H](NC(=O)[C@H](CC(C)C)N(C)C(=O)CN(C)C(=O)[C@H](CC)NC1=O)C(C)C

InChI

InChIKey=PMATZTZNYRCHOR-CGLBZJNRSA-N
InChI=1S/C62H111N11O12/c1-25-27-28-40(15)52(75)51-56(79)65-43(26-2)58(81)67(18)33-48(74)68(19)44(29-34(3)4)55(78)66-49(38(11)12)61(84)69(20)45(30-35(5)6)54(77)63-41(16)53(76)64-42(17)57(80)70(21)46(31-36(7)8)59(82)71(22)47(32-37(9)10)60(83)72(23)50(39(13)14)62(85)73(51)24/h25,27,34-47,49-52,75H,26,28-33H2,1-24H3,(H,63,77)(H,64,76)(H,65,79)(H,66,78)/b27-25+/t40-,41+,42-,43+,44+,45+,46+,47+,49+,50+,51+,52-/m1/s1

HIDE SMILES / InChI

Molecular Formula C62H111N11O12
Molecular Weight 1202.6112
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 12 / 12
E/Z Centers 1
Optical Activity UNSPECIFIED

Cyclosporins are cyclic polypeptide macrolides that were originally derived from the soil fungus Tolypocladium inflatum. Cyclosporine (also known as cyclosporine A) was discovered by Sandoz and developed for the tretment of immune disorders. The drug was approved by FDA for such diseases as Rheumatoid Arthritis, Psoriasis (Neoral), Keratoconjunctivitis sicca (Restasis) and prevention of transplant rejections (Neoral and Sandimmune). Cyclosporine’s primary immunosuppressive mechanism of action is inhibition of T-lymphocyte function. Upon administration cyclosporine binds to cyclophilin A and thus inhibits calcineurin, leading to immune system suppression.

CNS Activity

Curator's Comment: Cyclosporine was shown to cause neurotoxicty.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
36.8 nM [Kd]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
RESTASIS

Approved Use

Restasis is a calcineurin inhibitor immunosuppressant indicated to increase tear production in patients whose tear production is presumed to be suppressed due to ocular inflammation associated with keratoconjunctivitis sicca. Increased tear production was not seen in patients currently taking topical anti-inflammatory drugs or using punctal plugs.

Launch Date

1.06574401E12
Preventing
SANDIMMUNE

Approved Use

Sandimmune (cyclosporine) is indicated for the prophylaxis of organ rejection in kidney, liver, and heart allogeneic transplants. It is always to be used with adrenal corticosteroids. The drug may also be used in the treatment of chronic rejection in patients previously treated with other immunosuppressive agents.

Launch Date

4.37615985E11
Primary
NEORAL

Approved Use

Neoral is indicated for the treatment of patients with severe active, rheumatoid arthritis where the disease has not adequately responded to methotrexate. Neoral can be used in combination with methotrexate in rheumatoid arthritis patients who do not respond adequately to methotrexate alone.

Launch Date

8.0567999E11
Primary
NEORAL

Approved Use

Neoral is indicated for the treatment of adult, nonimmunocompromised patients with severe (i.e., extensive and/or disabling), recalcitrant, plaque psoriasis who have failed to respond to at least one systemic therapy (e.g., PUVA, retinoids, or methotrexate) or in patients for whom other systemic therapies are contraindicated, or cannot be tolerated.

Launch Date

8.0567999E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
1220 ng/mL
5.26 mg/kg single, oral
dose: 5.26 mg/kg
route of administration: Oral
experiment type: SINGLE
co-administered:
CYCLOSPORINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
3301 ng × h/mL
5.26 mg/kg single, oral
dose: 5.26 mg/kg
route of administration: Oral
experiment type: SINGLE
co-administered:
CYCLOSPORINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
6 h
300 mg single, oral
dose: 300 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CYCLOSPORINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
4 mg/kg 1 times / day multiple, intravenous
Dose: 4 mg/kg, 1 times / day
Route: intravenous
Route: multiple
Dose: 4 mg/kg, 1 times / day
Sources:
unhealthy, 36.7 years (range: 20–67 years)
n = 15
Health Status: unhealthy
Condition: Ulcerative Colitis
Age Group: 36.7 years (range: 20–67 years)
Sex: M+F
Population Size: 15
Sources:
Other AEs: Hypertension, Superficial thrombophlebitis...
Other AEs:
Hypertension (1 patient)
Superficial thrombophlebitis (1 patient)
Headache (2 patients)
Vomiting (1 patient)
Hypokalemia (4 patients)
Hypomagnesemia (2 patients)
Myalgia (2 patients)
Sources:
0.09 % 2 times / day multiple, ophthalmic
Recommended
Dose: 0.09 %, 2 times / day
Route: ophthalmic
Route: multiple
Dose: 0.09 %, 2 times / day
Sources: Page: p. 34
unhealthy, 61.9 years (range: 23-91 years)
n = 151
Health Status: unhealthy
Age Group: 61.9 years (range: 23-91 years)
Sex: M+F
Population Size: 151
Sources: Page: p. 34
Disc. AE: Musculoskeletal disorder, Connective tissue disorders...
Other AEs: Throat irritation...
AEs leading to
discontinuation/dose reduction:
Musculoskeletal disorder (moderate, 1 patient)
Connective tissue disorders (moderate, 1 patient)
General system disorders NEC (grade 1-2, 11 patient)
Instillation site pain (mild, 11 patient)
Instillation site pruritus (mild, 1 patient)
Candida infection (moderate, 1 patient)
Macular fibrosis (mild, 1 patient)
Sinusitis (mild, 1 patient)
Vision blurred (mild, 1 patient)
Eye irritation (mild, 1 patient)
Conjunctival hyperemia (moderate, 1 patient)
Foreign body sensation in eyes (severe, 1 patient)
Headache (grade 1-2, 2 patients)
Eye pain (mild, 2 patients)
Other AEs:
Throat irritation (mild, 1 patient)
Sources: Page: p. 34
10 g single, oral
Highest studied dose
unhealthy, adult
Other AEs: Vomiting, Drowsiness...
Other AEs:
Vomiting
Drowsiness
Headache
Tachycardia
Impaired renal function (grade 2)
Sources:
3 mg/kg 1 times / day steady, oral (total daily dose)
Dose: 3 mg/kg, 1 times / day
Route: oral
Route: steady
Dose: 3 mg/kg, 1 times / day
Sources:
unhealthy
n = 8
Health Status: unhealthy
Condition: Chronic Obstructive Pulmonary Disease
Population Size: 8
Sources:
Other AEs: Renal insufficiency, Gastrointestinal upset...
Other AEs:
Renal insufficiency (below serious, 4 patients)
Gastrointestinal upset (below serious, 4 patients)
Hyperkalemia (below serious, 2 patients)
Hypertension (below serious, 1 patient)
Tremor (below serious, 1 patient)
Cramp muscle (below serious, 1 patient)
Sources:
5 mg/kg 2 times / week steady, oral (total daily dose)
Dose: 5 mg/kg, 2 times / week
Route: oral
Route: steady
Dose: 5 mg/kg, 2 times / week
Sources:
unhealthy
n = 160
Health Status: unhealthy
Condition: Chronic Plaque Psoriasis
Population Size: 160
Sources:
Other AEs: Breast mass, Abdominal pain upper...
Other AEs:
Breast mass (serious, 1 patient)
Abdominal pain upper (below serious, 12 patients)
Hypertriglyceridaemia (below serious, 8 patients)
Sources:
AEs

AEs

AESignificanceDosePopulation
Hypertension 1 patient
4 mg/kg 1 times / day multiple, intravenous
Dose: 4 mg/kg, 1 times / day
Route: intravenous
Route: multiple
Dose: 4 mg/kg, 1 times / day
Sources:
unhealthy, 36.7 years (range: 20–67 years)
n = 15
Health Status: unhealthy
Condition: Ulcerative Colitis
Age Group: 36.7 years (range: 20–67 years)
Sex: M+F
Population Size: 15
Sources:
Superficial thrombophlebitis 1 patient
4 mg/kg 1 times / day multiple, intravenous
Dose: 4 mg/kg, 1 times / day
Route: intravenous
Route: multiple
Dose: 4 mg/kg, 1 times / day
Sources:
unhealthy, 36.7 years (range: 20–67 years)
n = 15
Health Status: unhealthy
Condition: Ulcerative Colitis
Age Group: 36.7 years (range: 20–67 years)
Sex: M+F
Population Size: 15
Sources:
Vomiting 1 patient
4 mg/kg 1 times / day multiple, intravenous
Dose: 4 mg/kg, 1 times / day
Route: intravenous
Route: multiple
Dose: 4 mg/kg, 1 times / day
Sources:
unhealthy, 36.7 years (range: 20–67 years)
n = 15
Health Status: unhealthy
Condition: Ulcerative Colitis
Age Group: 36.7 years (range: 20–67 years)
Sex: M+F
Population Size: 15
Sources:
Headache 2 patients
4 mg/kg 1 times / day multiple, intravenous
Dose: 4 mg/kg, 1 times / day
Route: intravenous
Route: multiple
Dose: 4 mg/kg, 1 times / day
Sources:
unhealthy, 36.7 years (range: 20–67 years)
n = 15
Health Status: unhealthy
Condition: Ulcerative Colitis
Age Group: 36.7 years (range: 20–67 years)
Sex: M+F
Population Size: 15
Sources:
Hypomagnesemia 2 patients
4 mg/kg 1 times / day multiple, intravenous
Dose: 4 mg/kg, 1 times / day
Route: intravenous
Route: multiple
Dose: 4 mg/kg, 1 times / day
Sources:
unhealthy, 36.7 years (range: 20–67 years)
n = 15
Health Status: unhealthy
Condition: Ulcerative Colitis
Age Group: 36.7 years (range: 20–67 years)
Sex: M+F
Population Size: 15
Sources:
Myalgia 2 patients
4 mg/kg 1 times / day multiple, intravenous
Dose: 4 mg/kg, 1 times / day
Route: intravenous
Route: multiple
Dose: 4 mg/kg, 1 times / day
Sources:
unhealthy, 36.7 years (range: 20–67 years)
n = 15
Health Status: unhealthy
Condition: Ulcerative Colitis
Age Group: 36.7 years (range: 20–67 years)
Sex: M+F
Population Size: 15
Sources:
Hypokalemia 4 patients
4 mg/kg 1 times / day multiple, intravenous
Dose: 4 mg/kg, 1 times / day
Route: intravenous
Route: multiple
Dose: 4 mg/kg, 1 times / day
Sources:
unhealthy, 36.7 years (range: 20–67 years)
n = 15
Health Status: unhealthy
Condition: Ulcerative Colitis
Age Group: 36.7 years (range: 20–67 years)
Sex: M+F
Population Size: 15
Sources:
General system disorders NEC grade 1-2, 11 patient
Disc. AE
0.09 % 2 times / day multiple, ophthalmic
Recommended
Dose: 0.09 %, 2 times / day
Route: ophthalmic
Route: multiple
Dose: 0.09 %, 2 times / day
Sources: Page: p. 34
unhealthy, 61.9 years (range: 23-91 years)
n = 151
Health Status: unhealthy
Age Group: 61.9 years (range: 23-91 years)
Sex: M+F
Population Size: 151
Sources: Page: p. 34
Headache grade 1-2, 2 patients
Disc. AE
0.09 % 2 times / day multiple, ophthalmic
Recommended
Dose: 0.09 %, 2 times / day
Route: ophthalmic
Route: multiple
Dose: 0.09 %, 2 times / day
Sources: Page: p. 34
unhealthy, 61.9 years (range: 23-91 years)
n = 151
Health Status: unhealthy
Age Group: 61.9 years (range: 23-91 years)
Sex: M+F
Population Size: 151
Sources: Page: p. 34
Throat irritation mild, 1 patient
0.09 % 2 times / day multiple, ophthalmic
Recommended
Dose: 0.09 %, 2 times / day
Route: ophthalmic
Route: multiple
Dose: 0.09 %, 2 times / day
Sources: Page: p. 34
unhealthy, 61.9 years (range: 23-91 years)
n = 151
Health Status: unhealthy
Age Group: 61.9 years (range: 23-91 years)
Sex: M+F
Population Size: 151
Sources: Page: p. 34
Eye irritation mild, 1 patient
Disc. AE
0.09 % 2 times / day multiple, ophthalmic
Recommended
Dose: 0.09 %, 2 times / day
Route: ophthalmic
Route: multiple
Dose: 0.09 %, 2 times / day
Sources: Page: p. 34
unhealthy, 61.9 years (range: 23-91 years)
n = 151
Health Status: unhealthy
Age Group: 61.9 years (range: 23-91 years)
Sex: M+F
Population Size: 151
Sources: Page: p. 34
Instillation site pruritus mild, 1 patient
Disc. AE
0.09 % 2 times / day multiple, ophthalmic
Recommended
Dose: 0.09 %, 2 times / day
Route: ophthalmic
Route: multiple
Dose: 0.09 %, 2 times / day
Sources: Page: p. 34
unhealthy, 61.9 years (range: 23-91 years)
n = 151
Health Status: unhealthy
Age Group: 61.9 years (range: 23-91 years)
Sex: M+F
Population Size: 151
Sources: Page: p. 34
Macular fibrosis mild, 1 patient
Disc. AE
0.09 % 2 times / day multiple, ophthalmic
Recommended
Dose: 0.09 %, 2 times / day
Route: ophthalmic
Route: multiple
Dose: 0.09 %, 2 times / day
Sources: Page: p. 34
unhealthy, 61.9 years (range: 23-91 years)
n = 151
Health Status: unhealthy
Age Group: 61.9 years (range: 23-91 years)
Sex: M+F
Population Size: 151
Sources: Page: p. 34
Sinusitis mild, 1 patient
Disc. AE
0.09 % 2 times / day multiple, ophthalmic
Recommended
Dose: 0.09 %, 2 times / day
Route: ophthalmic
Route: multiple
Dose: 0.09 %, 2 times / day
Sources: Page: p. 34
unhealthy, 61.9 years (range: 23-91 years)
n = 151
Health Status: unhealthy
Age Group: 61.9 years (range: 23-91 years)
Sex: M+F
Population Size: 151
Sources: Page: p. 34
Vision blurred mild, 1 patient
Disc. AE
0.09 % 2 times / day multiple, ophthalmic
Recommended
Dose: 0.09 %, 2 times / day
Route: ophthalmic
Route: multiple
Dose: 0.09 %, 2 times / day
Sources: Page: p. 34
unhealthy, 61.9 years (range: 23-91 years)
n = 151
Health Status: unhealthy
Age Group: 61.9 years (range: 23-91 years)
Sex: M+F
Population Size: 151
Sources: Page: p. 34
Instillation site pain mild, 11 patient
Disc. AE
0.09 % 2 times / day multiple, ophthalmic
Recommended
Dose: 0.09 %, 2 times / day
Route: ophthalmic
Route: multiple
Dose: 0.09 %, 2 times / day
Sources: Page: p. 34
unhealthy, 61.9 years (range: 23-91 years)
n = 151
Health Status: unhealthy
Age Group: 61.9 years (range: 23-91 years)
Sex: M+F
Population Size: 151
Sources: Page: p. 34
Eye pain mild, 2 patients
Disc. AE
0.09 % 2 times / day multiple, ophthalmic
Recommended
Dose: 0.09 %, 2 times / day
Route: ophthalmic
Route: multiple
Dose: 0.09 %, 2 times / day
Sources: Page: p. 34
unhealthy, 61.9 years (range: 23-91 years)
n = 151
Health Status: unhealthy
Age Group: 61.9 years (range: 23-91 years)
Sex: M+F
Population Size: 151
Sources: Page: p. 34
Candida infection moderate, 1 patient
Disc. AE
0.09 % 2 times / day multiple, ophthalmic
Recommended
Dose: 0.09 %, 2 times / day
Route: ophthalmic
Route: multiple
Dose: 0.09 %, 2 times / day
Sources: Page: p. 34
unhealthy, 61.9 years (range: 23-91 years)
n = 151
Health Status: unhealthy
Age Group: 61.9 years (range: 23-91 years)
Sex: M+F
Population Size: 151
Sources: Page: p. 34
Conjunctival hyperemia moderate, 1 patient
Disc. AE
0.09 % 2 times / day multiple, ophthalmic
Recommended
Dose: 0.09 %, 2 times / day
Route: ophthalmic
Route: multiple
Dose: 0.09 %, 2 times / day
Sources: Page: p. 34
unhealthy, 61.9 years (range: 23-91 years)
n = 151
Health Status: unhealthy
Age Group: 61.9 years (range: 23-91 years)
Sex: M+F
Population Size: 151
Sources: Page: p. 34
Connective tissue disorders moderate, 1 patient
Disc. AE
0.09 % 2 times / day multiple, ophthalmic
Recommended
Dose: 0.09 %, 2 times / day
Route: ophthalmic
Route: multiple
Dose: 0.09 %, 2 times / day
Sources: Page: p. 34
unhealthy, 61.9 years (range: 23-91 years)
n = 151
Health Status: unhealthy
Age Group: 61.9 years (range: 23-91 years)
Sex: M+F
Population Size: 151
Sources: Page: p. 34
Musculoskeletal disorder moderate, 1 patient
Disc. AE
0.09 % 2 times / day multiple, ophthalmic
Recommended
Dose: 0.09 %, 2 times / day
Route: ophthalmic
Route: multiple
Dose: 0.09 %, 2 times / day
Sources: Page: p. 34
unhealthy, 61.9 years (range: 23-91 years)
n = 151
Health Status: unhealthy
Age Group: 61.9 years (range: 23-91 years)
Sex: M+F
Population Size: 151
Sources: Page: p. 34
Foreign body sensation in eyes severe, 1 patient
Disc. AE
0.09 % 2 times / day multiple, ophthalmic
Recommended
Dose: 0.09 %, 2 times / day
Route: ophthalmic
Route: multiple
Dose: 0.09 %, 2 times / day
Sources: Page: p. 34
unhealthy, 61.9 years (range: 23-91 years)
n = 151
Health Status: unhealthy
Age Group: 61.9 years (range: 23-91 years)
Sex: M+F
Population Size: 151
Sources: Page: p. 34
Drowsiness
10 g single, oral
Highest studied dose
unhealthy, adult
Headache
10 g single, oral
Highest studied dose
unhealthy, adult
Tachycardia
10 g single, oral
Highest studied dose
unhealthy, adult
Vomiting
10 g single, oral
Highest studied dose
unhealthy, adult
Impaired renal function grade 2
10 g single, oral
Highest studied dose
unhealthy, adult
Cramp muscle below serious, 1 patient
3 mg/kg 1 times / day steady, oral (total daily dose)
Dose: 3 mg/kg, 1 times / day
Route: oral
Route: steady
Dose: 3 mg/kg, 1 times / day
Sources:
unhealthy
n = 8
Health Status: unhealthy
Condition: Chronic Obstructive Pulmonary Disease
Population Size: 8
Sources:
Hypertension below serious, 1 patient
3 mg/kg 1 times / day steady, oral (total daily dose)
Dose: 3 mg/kg, 1 times / day
Route: oral
Route: steady
Dose: 3 mg/kg, 1 times / day
Sources:
unhealthy
n = 8
Health Status: unhealthy
Condition: Chronic Obstructive Pulmonary Disease
Population Size: 8
Sources:
Tremor below serious, 1 patient
3 mg/kg 1 times / day steady, oral (total daily dose)
Dose: 3 mg/kg, 1 times / day
Route: oral
Route: steady
Dose: 3 mg/kg, 1 times / day
Sources:
unhealthy
n = 8
Health Status: unhealthy
Condition: Chronic Obstructive Pulmonary Disease
Population Size: 8
Sources:
Hyperkalemia below serious, 2 patients
3 mg/kg 1 times / day steady, oral (total daily dose)
Dose: 3 mg/kg, 1 times / day
Route: oral
Route: steady
Dose: 3 mg/kg, 1 times / day
Sources:
unhealthy
n = 8
Health Status: unhealthy
Condition: Chronic Obstructive Pulmonary Disease
Population Size: 8
Sources:
Gastrointestinal upset below serious, 4 patients
3 mg/kg 1 times / day steady, oral (total daily dose)
Dose: 3 mg/kg, 1 times / day
Route: oral
Route: steady
Dose: 3 mg/kg, 1 times / day
Sources:
unhealthy
n = 8
Health Status: unhealthy
Condition: Chronic Obstructive Pulmonary Disease
Population Size: 8
Sources:
Renal insufficiency below serious, 4 patients
3 mg/kg 1 times / day steady, oral (total daily dose)
Dose: 3 mg/kg, 1 times / day
Route: oral
Route: steady
Dose: 3 mg/kg, 1 times / day
Sources:
unhealthy
n = 8
Health Status: unhealthy
Condition: Chronic Obstructive Pulmonary Disease
Population Size: 8
Sources:
Abdominal pain upper below serious, 12 patients
5 mg/kg 2 times / week steady, oral (total daily dose)
Dose: 5 mg/kg, 2 times / week
Route: oral
Route: steady
Dose: 5 mg/kg, 2 times / week
Sources:
unhealthy
n = 160
Health Status: unhealthy
Condition: Chronic Plaque Psoriasis
Population Size: 160
Sources:
Hypertriglyceridaemia below serious, 8 patients
5 mg/kg 2 times / week steady, oral (total daily dose)
Dose: 5 mg/kg, 2 times / week
Route: oral
Route: steady
Dose: 5 mg/kg, 2 times / week
Sources:
unhealthy
n = 160
Health Status: unhealthy
Condition: Chronic Plaque Psoriasis
Population Size: 160
Sources:
Breast mass serious, 1 patient
5 mg/kg 2 times / week steady, oral (total daily dose)
Dose: 5 mg/kg, 2 times / week
Route: oral
Route: steady
Dose: 5 mg/kg, 2 times / week
Sources:
unhealthy
n = 160
Health Status: unhealthy
Condition: Chronic Plaque Psoriasis
Population Size: 160
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG


Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
no
no
no
yes [IC50 0.05 uM]
yes [IC50 0.1 uM]
yes [IC50 0.2 uM]
yes [IC50 2 uM]
yes [IC50 23 uM]
yes [IC50 4.5 uM]
yes [IC50 48 uM]
yes
yes
yes
yes
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
major
minor
minor
minor
no
no
no
no
no
no
no
yes
yes
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Relation between long-term steroid treatment after heart transplantation, hypofibrinolysis and myocardial microthrombi generation.
1999 Jul
Cyclosporin A and imipenem associated seizure activity in allogeneic bone marrow transplantation patients.
1999 Oct
Neuronal survival activity of s100betabeta is enhanced by calcineurin inhibitors and requires activation of NF-kappaB.
1999 Sep
Cyclosporine withdrawal in stable renal transplant recipients after azathioprine-mycophenolate mofetil conversion.
2000 Dec
Suppressive effects of cyclosporin A and FK-506 on superoxide generation in human polymorphonuclear leukocytes primed by tumor necrosis factor alpha.
2000 Dec
Calcineurin-mediated hypertrophy protects cardiomyocytes from apoptosis in vitro and in vivo: An apoptosis-independent model of dilated heart failure.
2000 Feb 18
Up-regulation of multidrug resistance P-glycoprotein via nuclear factor-kappaB activation protects kidney proximal tubule cells from cadmium- and reactive oxygen species-induced apoptosis.
2000 Jan 21
Phenytoin and cyclosporin A suppress the expression of MMP-1, TIMP-1, and cathepsin L, but not cathepsin B in cultured gingival fibroblasts.
2000 Jun
Tacrolimus has less fibrogenic potential than cyclosporin A in a model of renal ischaemia-reperfusion injury.
2000 Nov
Calmodulin kinases II and IV and calcineurin are involved in leukemia inhibitory factor-induced cardiac hypertrophy in rats.
2000 Nov 10
Conversion to rapamycin immunosuppression in renal transplant recipients: report of an initial experience.
2000 Oct 27
Calcineurin-inhibitor related nephrotoxicity- reversibility in paediatric liver transplant recipients.
2001 Aug 27
Bone marrow aplasia after pipobroman: an immune-mediated mechanism?
2001 Dec
Cyclosporin-induced hypertension.
2001 Dec
Sirolimus interferes with the innate response to bacterial products in human whole blood by attenuation of IL-10 production.
2001 Feb
Characterization of the mouse bile salt export pump overexpressed in the baculovirus system.
2001 May
Fatal acute hepatic failure induced by danazol in a patient with endometriosis and aplastic anemia.
2001 Nov
Severe neurotoxicity of tacrolimus (FK506) after renal transplantation: two case reports.
2001 Nov-Dec
Cyclosporin A-induced encephalopathy after allogeneic bone marrow transplantation with prevention of graft-versus-host disease by tacrolimus.
2001 Oct
Use of rapamycin in a transplant patient who developed cyclosporin neurotoxicity.
2001 Oct
Correlates of acute renal failure in patients receiving parenteral amphotericin B.
2001 Oct
Silencer activity of NFATc2 in the interleukin-12 receptor beta 2 proximal promoter in human T helper cells.
2001 Sep 14
Calcineurin-GATA4 pathway is involved in beta-adrenergic agonist-responsive endothelin-1 transcription in cardiac myocytes.
2001 Sep 14
Myelodysplastic syndrome complicated by autoimmune hemolytic anemia: remission of refractory anemia following mycophenolate mofetil.
2002 Dec
Sirolimus (Rapamune) in renal transplantation.
2002 Nov
Oxidative stress in kidney transplant patients with calcineurin inhibitor-induced hypertension: effect of ramipril.
2002 Oct
Pimecrolimus inhibits up-regulation of OX40 and synthesis of inflammatory cytokines upon secondary T cell activation by allogeneic dendritic cells.
2002 Oct
Influence of different chemicals on MDR-1 P-glycoprotein expression and activity in the HK-2 proximal tubular cell line.
2002 Sep 1
Patents

Sample Use Guides

Organs transplantation: the initial oral dose of cyclosporine (Sandimmune) should be given 4 to 12 hours prior to transplantation as a single dose of 15 mg/kg. Rheumatoid Arthritis, Psoriasis: the initial dose of cyclosporine (Neoral) is 2.5 mg/kg/day, taken twice daily as a divided (BID) oral dose. Keratoconjunctivitis sicca: instill one drom twice a day in each eye, approximately 12 hours apart.
Route of Administration: Other
Human CD4+CD25+ cells isolated from healthy donors were cultured in the presence of 40 or 400 ng/mL of cyclosporine. The suppressive activity of Treg was assessed in mixed leukocyte reactions (MLR) using CD25+ and autologous activated peripheral blood mononuclear cells (PBMC). The drug inhibited the proliferative capacity of PBMC and CD4+CD25+ Treg in a dose-dependent manner.
Substance Class Chemical
Created
by admin
on Wed Jul 05 23:20:13 UTC 2023
Edited
by admin
on Wed Jul 05 23:20:13 UTC 2023
Record UNII
83HN0GTJ6D
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CYCLOSPORINE
GREEN BOOK   HSDB   ORANGE BOOK   USAN   USP   USP-RS   VANDF  
USAN  
Official Name English
CYCLOSPORIN A [MI]
Common Name English
CICLOSPORINUM [WHO-IP LATIN]
Common Name English
EQUORAL
Common Name English
CYCLOSPORIN
Common Name English
CYCLOSPORINE [GREEN BOOK]
Common Name English
CICLOSPORIN A
Common Name English
CICLOSPORIN [EP MONOGRAPH]
Common Name English
GENGRAF
Brand Name English
RAMIHYPHIN A
Common Name English
(R-(R*,R*-(E)))-CYCLIC(L-ALANYL-D-ALANYL-N-METHYL-L-LEUCYL-N-METHYL-L-LEUCYL-N-METHYL-L-VALYL-3-HYDROXY-N,4-DIMETHYL-L-2-AMINO-6-OCTENOYL-L-.ALPHA.-AMINOBUTYRYL-N-METHYLGLYCYL-N-METHYL-L-LEUCYL-L-VALYL-N-METHYL-L-LEUCYL)
Common Name English
NSC-290193
Code English
NEOPLANTA
Common Name English
SANDIMMUNE
Brand Name English
NEORAL
Brand Name English
SDZ-OXL-400
Code English
MITOGARD
Brand Name English
VEVYE
Brand Name English
OL-27-400
Code English
NEUROSTAT
Brand Name English
CYCLOSPORINE [USP-RS]
Common Name English
ATOPICA
Brand Name English
CYCLOSPORINE [HSDB]
Common Name English
OPTIMMUNE
Brand Name English
CYCLO(((E)-(2S,3R,4R)-3-HYDROXY-4-METHYL-2-(METHYLAMINO)-6-OCTENOYL)-L-2-AMINOBUTYRYL-N-METHYLGLYCYL-N-METHYL-L-LEUCYL-L-VALYL-N-METHYL-L-LEUCYL-L-ALANYL-D-ALANYL-N-METHYL-L-LEUCYL-N-METHYL-L-LEUCYL-N-METHYL-L-VALYL)
Common Name English
CYCLOSPORINE MICROEMULSION
Common Name English
VERKAZIA
Brand Name English
IKERVIS
Brand Name English
CYCLOSPORINE [IARC]
Common Name English
CYCLOSPORINE, MODIFIED
Common Name English
CYCLOSPORINE [VANDF]
Common Name English
ANTIBIOTIC S-7481F1
Code English
CICLOSPORIN [JAN]
Common Name English
CYCLOSPORINE [USAN]
Common Name English
CICLOSPORIN
EP   INN   MART.   WHO-DD   WHO-IP  
INN  
Official Name English
ciclosporin [INN]
Common Name English
CYCLOSPORINE [USP IMPURITY]
Common Name English
CYCLOSPORINE [USP MONOGRAPH]
Common Name English
CYCLOSPORIN A
MI  
Common Name English
SANG-35
Code English
27-400
Code English
CEQUA
Brand Name English
CYCLOSPORINE [ORANGE BOOK]
Common Name English
Ciclosporin [WHO-DD]
Common Name English
CYCLOSPORINE A
Common Name English
CICLOSPORIN [WHO-IP]
Common Name English
RESTASIS
Brand Name English
ZINOGRAF ME
Common Name English
SANDIMMUN
Brand Name English
CICLOSPORIN [MART.]
Common Name English
Classification Tree Code System Code
WHO-VATC QS01XA18
Created by admin on Wed Jul 05 23:20:13 UTC 2023 , Edited by admin on Wed Jul 05 23:20:13 UTC 2023
FDA ORPHAN DRUG 252207
Created by admin on Wed Jul 05 23:20:13 UTC 2023 , Edited by admin on Wed Jul 05 23:20:13 UTC 2023
FDA ORPHAN DRUG 252107
Created by admin on Wed Jul 05 23:20:13 UTC 2023 , Edited by admin on Wed Jul 05 23:20:13 UTC 2023
FDA ORPHAN DRUG 224106
Created by admin on Wed Jul 05 23:20:13 UTC 2023 , Edited by admin on Wed Jul 05 23:20:13 UTC 2023
NCI_THESAURUS C574
Created by admin on Wed Jul 05 23:20:13 UTC 2023 , Edited by admin on Wed Jul 05 23:20:13 UTC 2023
FDA ORPHAN DRUG 319710
Created by admin on Wed Jul 05 23:20:13 UTC 2023 , Edited by admin on Wed Jul 05 23:20:13 UTC 2023
FDA ORPHAN DRUG 138500
Created by admin on Wed Jul 05 23:20:13 UTC 2023 , Edited by admin on Wed Jul 05 23:20:13 UTC 2023
FDA ORPHAN DRUG 58991
Created by admin on Wed Jul 05 23:20:13 UTC 2023 , Edited by admin on Wed Jul 05 23:20:13 UTC 2023
FDA ORPHAN DRUG 176303
Created by admin on Wed Jul 05 23:20:13 UTC 2023 , Edited by admin on Wed Jul 05 23:20:13 UTC 2023
FDA ORPHAN DRUG 29988
Created by admin on Wed Jul 05 23:20:13 UTC 2023 , Edited by admin on Wed Jul 05 23:20:13 UTC 2023
FDA ORPHAN DRUG 275108
Created by admin on Wed Jul 05 23:20:13 UTC 2023 , Edited by admin on Wed Jul 05 23:20:13 UTC 2023
NDF-RT N0000175458
Created by admin on Wed Jul 05 23:20:13 UTC 2023 , Edited by admin on Wed Jul 05 23:20:13 UTC 2023
FDA ORPHAN DRUG 254807
Created by admin on Wed Jul 05 23:20:13 UTC 2023 , Edited by admin on Wed Jul 05 23:20:13 UTC 2023
EMA ASSESSMENT REPORTS IKERVIS (AUTHORIZED: CORNEAL DISEASES)
Created by admin on Wed Jul 05 23:20:13 UTC 2023 , Edited by admin on Wed Jul 05 23:20:13 UTC 2023
FDA ORPHAN DRUG 273308
Created by admin on Wed Jul 05 23:20:13 UTC 2023 , Edited by admin on Wed Jul 05 23:20:13 UTC 2023
LIVERTOX NBK548753
Created by admin on Wed Jul 05 23:20:13 UTC 2023 , Edited by admin on Wed Jul 05 23:20:13 UTC 2023
WHO-ESSENTIAL MEDICINES LIST 8.1
Created by admin on Wed Jul 05 23:20:13 UTC 2023 , Edited by admin on Wed Jul 05 23:20:13 UTC 2023
WHO-ATC S01XA18
Created by admin on Wed Jul 05 23:20:13 UTC 2023 , Edited by admin on Wed Jul 05 23:20:13 UTC 2023
CFR 21 CFR 862.1235
Created by admin on Wed Jul 05 23:20:13 UTC 2023 , Edited by admin on Wed Jul 05 23:20:13 UTC 2023
FDA ORPHAN DRUG 194704
Created by admin on Wed Jul 05 23:20:13 UTC 2023 , Edited by admin on Wed Jul 05 23:20:13 UTC 2023
NCI_THESAURUS C1744
Created by admin on Wed Jul 05 23:20:13 UTC 2023 , Edited by admin on Wed Jul 05 23:20:13 UTC 2023
FDA ORPHAN DRUG 112798
Created by admin on Wed Jul 05 23:20:13 UTC 2023 , Edited by admin on Wed Jul 05 23:20:13 UTC 2023
NDF-RT N0000175457
Created by admin on Wed Jul 05 23:20:13 UTC 2023 , Edited by admin on Wed Jul 05 23:20:13 UTC 2023
FDA ORPHAN DRUG 239907
Created by admin on Wed Jul 05 23:20:13 UTC 2023 , Edited by admin on Wed Jul 05 23:20:13 UTC 2023
CFR 21 CFR 520.522
Created by admin on Wed Jul 05 23:20:13 UTC 2023 , Edited by admin on Wed Jul 05 23:20:13 UTC 2023
WHO-VATC QL04AD01
Created by admin on Wed Jul 05 23:20:13 UTC 2023 , Edited by admin on Wed Jul 05 23:20:13 UTC 2023
FDA ORPHAN DRUG 254907
Created by admin on Wed Jul 05 23:20:13 UTC 2023 , Edited by admin on Wed Jul 05 23:20:13 UTC 2023
FDA ORPHAN DRUG 180103
Created by admin on Wed Jul 05 23:20:13 UTC 2023 , Edited by admin on Wed Jul 05 23:20:13 UTC 2023
FDA ORPHAN DRUG 51790
Created by admin on Wed Jul 05 23:20:13 UTC 2023 , Edited by admin on Wed Jul 05 23:20:13 UTC 2023
NCI_THESAURUS C146638
Created by admin on Wed Jul 05 23:20:13 UTC 2023 , Edited by admin on Wed Jul 05 23:20:13 UTC 2023
WHO-ATC L04AD01
Created by admin on Wed Jul 05 23:20:13 UTC 2023 , Edited by admin on Wed Jul 05 23:20:13 UTC 2023
CFR 21 CFR 524.575
Created by admin on Wed Jul 05 23:20:13 UTC 2023 , Edited by admin on Wed Jul 05 23:20:13 UTC 2023
EU-Orphan Drug EU/3/06/415
Created by admin on Wed Jul 05 23:20:13 UTC 2023 , Edited by admin on Wed Jul 05 23:20:13 UTC 2023
Code System Code Type Description
WIKIPEDIA
CICLOSPORIN
Created by admin on Wed Jul 05 23:20:13 UTC 2023 , Edited by admin on Wed Jul 05 23:20:13 UTC 2023
PRIMARY
RS_ITEM_NUM
1158504
Created by admin on Wed Jul 05 23:20:13 UTC 2023 , Edited by admin on Wed Jul 05 23:20:13 UTC 2023
PRIMARY
INN
5086
Created by admin on Wed Jul 05 23:20:13 UTC 2023 , Edited by admin on Wed Jul 05 23:20:13 UTC 2023
PRIMARY
CAS
59865-13-3
Created by admin on Wed Jul 05 23:20:13 UTC 2023 , Edited by admin on Wed Jul 05 23:20:13 UTC 2023
PRIMARY
MESH
D016572
Created by admin on Wed Jul 05 23:20:13 UTC 2023 , Edited by admin on Wed Jul 05 23:20:13 UTC 2023
PRIMARY
IUPHAR
1024
Created by admin on Wed Jul 05 23:20:13 UTC 2023 , Edited by admin on Wed Jul 05 23:20:13 UTC 2023
PRIMARY
LACTMED
Cyclosporine
Created by admin on Wed Jul 05 23:20:13 UTC 2023 , Edited by admin on Wed Jul 05 23:20:13 UTC 2023
PRIMARY
NSC
290193
Created by admin on Wed Jul 05 23:20:13 UTC 2023 , Edited by admin on Wed Jul 05 23:20:13 UTC 2023
PRIMARY
DRUG CENTRAL
760
Created by admin on Wed Jul 05 23:20:13 UTC 2023 , Edited by admin on Wed Jul 05 23:20:13 UTC 2023
PRIMARY
EVMPD
SUB06250MIG
Created by admin on Wed Jul 05 23:20:13 UTC 2023 , Edited by admin on Wed Jul 05 23:20:13 UTC 2023
PRIMARY
FDA UNII
83HN0GTJ6D
Created by admin on Wed Jul 05 23:20:13 UTC 2023 , Edited by admin on Wed Jul 05 23:20:13 UTC 2023
PRIMARY
PUBCHEM
5284373
Created by admin on Wed Jul 05 23:20:13 UTC 2023 , Edited by admin on Wed Jul 05 23:20:13 UTC 2023
PRIMARY
RXCUI
3008
Created by admin on Wed Jul 05 23:20:13 UTC 2023 , Edited by admin on Wed Jul 05 23:20:13 UTC 2023
PRIMARY
DAILYMED
83HN0GTJ6D
Created by admin on Wed Jul 05 23:20:13 UTC 2023 , Edited by admin on Wed Jul 05 23:20:13 UTC 2023
PRIMARY
EVMPD
SUB129839
Created by admin on Wed Jul 05 23:20:13 UTC 2023 , Edited by admin on Wed Jul 05 23:20:13 UTC 2023
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
CYCLOSPORINE
Created by admin on Wed Jul 05 23:20:13 UTC 2023 , Edited by admin on Wed Jul 05 23:20:13 UTC 2023
PRIMARY Description: A white or almost white powder.Solubility: Practically insoluble in water; freely soluble in ethanol (~750 g/l) TS and dichloromethane R.Category: Immunosuppressant drug.Storage: Ciclosporin should be kept in a well-closed container, protected from light.
HSDB
6881
Created by admin on Wed Jul 05 23:20:13 UTC 2023 , Edited by admin on Wed Jul 05 23:20:13 UTC 2023
PRIMARY
RXCUI
236077
Created by admin on Wed Jul 05 23:20:13 UTC 2023 , Edited by admin on Wed Jul 05 23:20:13 UTC 2023
ALTERNATIVE
NDF-RT
N0000185503
Created by admin on Wed Jul 05 23:20:13 UTC 2023 , Edited by admin on Wed Jul 05 23:20:13 UTC 2023
PRIMARY P-Glycoprotein Inhibitors [MoA]
SMS_ID
100000092121
Created by admin on Wed Jul 05 23:20:13 UTC 2023 , Edited by admin on Wed Jul 05 23:20:13 UTC 2023
PRIMARY
CHEBI
4031
Created by admin on Wed Jul 05 23:20:13 UTC 2023 , Edited by admin on Wed Jul 05 23:20:13 UTC 2023
PRIMARY
DRUG BANK
DB00091
Created by admin on Wed Jul 05 23:20:13 UTC 2023 , Edited by admin on Wed Jul 05 23:20:13 UTC 2023
PRIMARY
NDF-RT
N0000182141
Created by admin on Wed Jul 05 23:20:13 UTC 2023 , Edited by admin on Wed Jul 05 23:20:13 UTC 2023
PRIMARY Cytochrome P450 3A4 Inhibitors [MoA]
RXCUI
484788
Created by admin on Wed Jul 05 23:20:13 UTC 2023 , Edited by admin on Wed Jul 05 23:20:13 UTC 2023
ALTERNATIVE
NCI_THESAURUS
C406
Created by admin on Wed Jul 05 23:20:13 UTC 2023 , Edited by admin on Wed Jul 05 23:20:13 UTC 2023
PRIMARY
MERCK INDEX
M4020
Created by admin on Wed Jul 05 23:20:13 UTC 2023 , Edited by admin on Wed Jul 05 23:20:13 UTC 2023
PRIMARY Merck Index
ChEMBL
CHEMBL160
Created by admin on Wed Jul 05 23:20:13 UTC 2023 , Edited by admin on Wed Jul 05 23:20:13 UTC 2023
PRIMARY
EPA CompTox
DTXSID0020365
Created by admin on Wed Jul 05 23:20:13 UTC 2023 , Edited by admin on Wed Jul 05 23:20:13 UTC 2023
PRIMARY
Related Record Type Details
TRANSPORTER -> INHIBITOR
can potentially be used for in vivo (clinical) studies
METABOLIC ENZYME -> SUBSTRATE
TRANSPORTER -> INHIBITOR
TARGET -> INHIBITOR
TRANSPORTER -> INHIBITOR
TRANSPORTER -> INHIBITOR
SUBSTRATE USED: Bromsulphthalein
TRANSPORTER -> SUBSTRATE
TARGET -> INHIBITOR
BINDING
DERIVATIVE -> PARENT
TRANSPORTER -> SUBSTRATE
TRANSPORTER -> INHIBITOR
TRANSPORTER -> INHIBITOR
TRANSPORTER -> INHIBITOR
substrate used: Amantinin, Bosentan, Bromsulphthalein (BSP), Rosuvastatin
DERIVATIVE -> PARENT
TRANSPORTER -> INHIBITOR
METABOLIC ENZYME -> SUBSTRATE
TRANSPORTER -> INHIBITOR
METABOLIC ENZYME -> INHIBITOR
Related Record Type Details
ACTIVE MOIETY