CYCLOSPORINE

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 Search

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/24341787 | http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/050573s041,050574s051,050625s055lbl.pdf | http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/050715s035,050716s038lbl.pdf | http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/050790s024s025lbl.pdf

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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Cyclophilin A 1 Target ID: CHEMBL1949 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24341787	Binding Agent 1064		36.8 nM [Kd]

Conditions

Condition	Modality	Highest Phase	Product
Keratoconjunctivitis sicca 2 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/050790s024s025lbl.pdf	Palliative	Approved 8429	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 2003
Organ rejection in kidney, liver, and heart allogeneic transplants 1 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/050573s041,050574s051,050625s055lbl.pdf	Preventing	Approved 8429	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 1983
Rheumatoid arthritis 316 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/050715s035,050716s038lbl.pdf	Primary	Approved 8429	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 1995
Psoriasis 84 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/050715s035,050716s038lbl.pdf	Primary	Approved 8429	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 1995

C_max

Value	Dose	Co-administered	Analyte	Population
1220 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/12118899	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

Value	Dose	Co-administered	Analyte	Population
3301 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/12118899	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

T_1/2

Value	Dose	Co-administered	Analyte	Population
6 h REVIEW https://www.ncbi.nlm.nih.gov/pubmed/3322675	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

Dose	Population	Adverse 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: https://pubmed.ncbi.nlm.nih.gov/11313301	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: https://pubmed.ncbi.nlm.nih.gov/11313301	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: https://pubmed.ncbi.nlm.nih.gov/11313301
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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210913Orig1s000MedR.pdf 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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210913Orig1s000MedR.pdf 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: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/210913Orig1s000MedR.pdf Page: p. 34
10 g single, oral Highest studied dose Dose: 10 g Route: oral Route: single Dose: 10 g Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/050573s041,050574s051,050625s055lbl.pdf	unhealthy, adult Health Status: unhealthy Age Group: adult Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/050573s041,050574s051,050625s055lbl.pdf	Other AEs: Vomiting, Drowsiness... Other AEs: Vomiting Drowsiness Headache Tachycardia Impaired renal function (grade 2) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/050573s041,050574s051,050625s055lbl.pdf
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: https://clinicaltrials.gov/ct2/show/NCT00974142	unhealthy n = 8 Health Status: unhealthy Condition: Chronic Obstructive Pulmonary Disease Population Size: 8 Sources: https://clinicaltrials.gov/ct2/show/NCT00974142	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: https://clinicaltrials.gov/ct2/show/NCT00974142
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: https://clinicaltrials.gov/ct2/show/NCT00438360	unhealthy n = 160 Health Status: unhealthy Condition: Chronic Plaque Psoriasis Population Size: 160 Sources: https://clinicaltrials.gov/ct2/show/NCT00438360	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: https://clinicaltrials.gov/ct2/show/NCT00438360

AEs

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1737			inhibitor 1612

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
UGT1A1 204 UGT1A4 77 UGT1A6 108 UGT2B7 146 UGT2B10 25 OATP1B1 788 OATP1B3 706 NTCP 34 BCRP 699 OATP2 4 MDR 1	UGT1A1 418 UGT1A3 422 UGT1A4 347 UGT1A6 307 UGT1A7 236 UGT1A8 283 UGT1A9 380 UGT1A10 291 UGT2B4 249 UGT2B7 389 UGT2B15 203 P-gp 1537	CYP1A1 108 CYP1A2 701 CYP2D1 2

Drug as perpetrator

Target	Modality	Activity
UGT1A6 141	inhibitor 3277 Sources: https://www.tandfonline.com/doi/full/10.3109/14756366.2010.518965 Page: -	no
UGT2B10 27	inhibitor 3277 Sources: https://www.tandfonline.com/doi/full/10.3109/14756366.2010.518965 Page: -	no
UGT2B7 157	inhibitor 3277 Sources: https://www.tandfonline.com/doi/full/10.3109/14756366.2010.518965 Page: -	no
OATP1B3 715	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/23881596/ Page: -	yes [IC50 0.05 uM]
OATP1B1 803	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/23881596/ Page: -	yes [IC50 0.1 uM]
OATP2 4	inhibitor 3277 Sources: https://jpet.aspetjournals.org/content/304/2/610.short Page: -	yes [IC50 0.2 uM]
BCRP 773	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/23881596/ Page: -	yes [IC50 2 uM]
UGT1A4 80	inhibitor 3277 Sources: https://www.tandfonline.com/doi/full/10.3109/14756366.2010.518965 Page: -	yes [IC50 23 uM]
NTCP 35	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/23881596/ Page: -	yes [IC50 4.5 uM]
UGT1A1 254	inhibitor 3277 Sources: https://www.tandfonline.com/doi/full/10.3109/14756366.2010.518965 Page: -	yes [IC50 48 uM]
CYP1A1 218	inducer 1573 Sources: https://pubmed.ncbi.nlm.nih.gov/8361996/ Page: -	yes
CYP1A2 1692	inducer 1573 Sources: https://pubmed.ncbi.nlm.nih.gov/8361996/ Page: -	yes
CYP2D1 8	inducer 1573 Sources: https://pubmed.ncbi.nlm.nih.gov/8361996/ Page: -	yes
MDR 1	inhibitor 3277 Sources: http://citeseerx.ist.psu.edu/viewdoc/download?doi=10.1.1.915.5144&rep=rep1&type=pdf Page: -	yes

Drug as victim

Target	Modality	Activity
UGT2B7 389	substrate 3367 Sources: https://www.sciencedirect.com/science/article/pii/S016882780100040X Page: -	major
UGT1A1 418	substrate 3367 Sources: https://www.sciencedirect.com/science/article/pii/S016882780100040X Page: -	minor
UGT1A10 291	substrate 3367 Sources: https://www.sciencedirect.com/science/article/pii/S016882780100040X Page: -	minor
UGT1A3 422	substrate 3367 Sources: https://www.sciencedirect.com/science/article/pii/S016882780100040X Page: -	minor
UGT1A4 347	substrate 3367 Sources: https://www.sciencedirect.com/science/article/pii/S016882780100040X Page: -	no
UGT1A6 307	substrate 3367 Sources: https://www.sciencedirect.com/science/article/pii/S016882780100040X Page: -	no
UGT1A7 236	substrate 3367 Sources: https://www.sciencedirect.com/science/article/pii/S016882780100040X Page: -	no
UGT1A8 283	substrate 3367 Sources: https://www.sciencedirect.com/science/article/pii/S016882780100040X Page: -	no
UGT1A9 380	substrate 3367 Sources: https://www.sciencedirect.com/science/article/pii/S016882780100040X Page: -	no
UGT2B15 203	substrate 3367 Sources: https://www.sciencedirect.com/science/article/pii/S016882780100040X Page: -	no
UGT2B4 249	substrate 3367 Sources: https://www.sciencedirect.com/science/article/pii/S016882780100040X Page: -	no
CYP3A4 1737	substrate 3367 Sources: https://link.springer.com/article/10.1007%2FBF03190040 Page: -	yes
P-gp 1537	substrate 3367 Sources: https://www.sciencedirect.com/science/article/pii/S0085253815520577 Page: -	yes

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 1647	inhibitor 1626 Sources: https://pubmed.ncbi.nlm.nih.gov/22128262/ Page: -

Sourcing

Vendor/Aggregator	ID	URL
3B Scientific (Wuhan) Corp	3B2-0266	http://www.3bsc.com/index/pro_info.php?id=19622
AA Blocks	AA005L8Q	https://www.aablocks.com/goods/Goods/detail?id=AA005L8Q
AHH Chemical co.,ltd	API-1252	http://www.ahhchemical.com/product/API-1252.html
AHH Chemical co.,ltd	MT-01094	http://www.ahhchemical.com/product/MT-01094.html
AK Scientific, Inc. (AKSCI)	J10181	http://www.aksci.com/item_detail.php?cat=J10181
AK Scientific, Inc. (AKSCI)	J90049	http://www.aksci.com/item_detail.php?cat=J90049
AK Scientific, Inc. (AKSCI)	Q333	http://www.aksci.com/item_detail.php?cat=Q333
Aaron Chemicals	AR005M0I	http://www.aaronchem.com/79217-60-0
AbMole Bioscience	M1831	http://www.abmole.com/products/cyclosporine-a.html
AbMole Bioscience	M5541	http://www.abmole.com/products/cyclosporine.html
Achemtek	0104-013119	http://www.achemtek.com/59865-13-3
Acorn PharmaTech	ACN-029253	http://www.acornpharmatech.com/
Adooq BioScience	A10260	https://www.adooq.com/cyclosporin-a.html
Alfa Chemistry	AP59865133-C	https://reagents.alfa-chemistry.com/product/cyclosporin-a-cas-59865-13-3-13792.html
Alfa Chemistry	AP59865133-A	https://reagents.alfa-chemistry.com/product/cyclosporin-a-ready-made-solution-cas-59865-13-3-13790.html
Alfa Chemistry	AP59865133-D	https://reagents.alfa-chemistry.com/product/cyclosporin-a-solution-cas-59865-13-3-13793.html
Alfa Chemistry	AP59865133-E	https://reagents.alfa-chemistry.com/product/cyclosporin-a-solution-cas-59865-13-3-13794.html
Alfa Chemistry	AP59865133-B	https://reagents.alfa-chemistry.com/product/cyclosporine-cas-59865-13-3-13791.html
Alsachim	950	http://www.alsachim.com/product-C2629-glo.bal-view.html
Ambinter	Amb1865584	http://www.ambinter.com/reference/1865584
ApexBio Technology	B1922	http://www.apexbt.com/cyclosporin-a.html
ApexBio Technology	A5938	http://www.apexbt.com/cyclosporine.html
Aurora Fine Chemicals LLC	A13.105.543	http://online.aurorafinechemicals.com/info?ID=A13.105.543
AvaChem Scientific	1968	http://www.avachem.com/productSearch.asp?1968
Avantor Inc	101096-750	https://us.vwr.com/store/catalog/product.jsp?catalog_number=101096-750
BOC Sciences	59865-13-3	https://www.bocsci.com/cyclosporine-cas-59865-13-3-item-84-300196.html
BioCrick	BCC4773	http://www.biocrick.com/Cyclosporin-A-BCC4773.html
BioCrick	BCC2559	http://www.biocrick.com/Cyclosporine-BCC2559.html
BioSynth	Q-200913	https://www.biosynth.com/en/products/chemical-intermediates/basic-intermediates/products/Q-200913.html
Biopurify Phytochemicals	BP0438	http://www.phytopurify.com/CyclosporinA-p-4184.html
Calbiochem	239835	http://www.emdbiosciences.com/product/239835
Chem Scene	CS-2761	http://www.chemscene.com/59865-13-3.html
ChemMol	2101379	http://www.chemmol.com/chemmol/2101379.html
ChemMol	49422981	http://www.chemmol.com/chemmol/49422981.html
Chemenu	CM119904	http://www.chemenu.com/products/CM119904
Chemspace	CSSB00161189749	https://chem-space.com/CSSB00161189749
Chemspace	CSSB02125554483	https://chem-space.com/CSSB02125554483
Chemspace	CSSS02125561432	https://chem-space.com/CSSS02125561432
Clearsynth	CS-O-06250	https://www.clearsynth.com/en/CSO06250.html
DC Chemicals	DC4115	http://www.dcchemicals.com/product_show-Cyclosporin_A.html
EMD Millipore	239835	http://www.emdbiosciences.com/product/239835
Excenen	EX-A4110	https://www.excenen.com/searchresultlist.php?id=EX-A4110
Glentham Life Sciences	GA6323	http://www.glentham.com/products/product/GA6323/
Hairui	HR132082	http://www.hairuichem.com/en/product/59865-13-3.html
Huateng Pharma	F80017934	http://en.huatengsci.com/product/Cyclosporin-A.html
LGC Standards	DRE-C11836300	https://www.lgcstandards.com/US/en/p/DRE-C11836300
LGC Standards	MM0241.00	https://www.lgcstandards.com/US/en/p/MM0241.00
Lab Network	LN01327074	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN01327074
MedChem Express	HY-B0579	https://www.medchemexpress.com/cyclosporin-a.html
MolPort	MolPort-000-760-988	https://www.molport.com/shop/molecule-link/MolPort-000-760-988
MolPort	MolPort-005-934-008	https://www.molport.com/shop/molecule-link/MolPort-005-934-008
MolPort	MolPort-006-705-994	https://www.molport.com/shop/molecule-link/MolPort-006-705-994
MolPort	MolPort-023-220-498	https://www.molport.com/shop/molecule-link/MolPort-023-220-498
OChem	2004	http://www.ocheminc.com/index.php?act=psearch&pid=865C133
Octagon Chemicals	API Cyclosporine 59865-13-3	https://octagonchem.com/products/apis/cyclosporine/
Parchem	10883	http://www.parchem.com/chemical-supplier-distributor/Cyclosporin-000883.aspx
Selleck Chemicals	S1514	http://www.selleckchem.com/products/Cyclosporine.html
Sigma-Aldrich	32425_SIAL	https://www.sigmaaldrich.com/catalog/product/sial/32425?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	C2163000_SIAL	https://www.sigmaaldrich.com/catalog/product/sial/c2163000?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	30024_SIGMA	https://www.sigmaaldrich.com/catalog/product/sigma/30024?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	C1832_SIGMA	https://www.sigmaaldrich.com/catalog/product/sigma/c1832?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	1158504_USP	https://www.sigmaaldrich.com/catalog/product/usp/1158504?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sinfoo Biotech	S061040	http://www.sinfoobiotech.com/product/1064443
TCI (Tokyo Chemical Industry)	C2408	http://www.tcichemicals.com/eshop/en/us/commodity/C2408/index.html
THE BioTek	bt-242573	https://www.thebiotek.com/product/peptides/bt-242573
TOKU-E Company	C042	http://www.toku-e.com/product/cyclosporin_a/
Tocris	1101	https://www.tocris.com/products/cyclosporin-a_1101
Vitas-M Laboratory	STK177328	http://www.request.vitasmlab.biz/index.php?option=com_search_stk&Itemid=22&stk=STK177328&?utm_source=pubchem&utm_medium=p_search_link&utm_campaign=pubchem_search&utm_content=pubchem_slink
VladaChem	VL265833-1G	https://www.vladachem.com/product.php?products=59865-13-3
Wuhan Atomole Chemicals Co., Ltd.	AT-12519	http://www.atomole.com/en/products-view.asp?id=2269
abcr GmbH	AB181158	http://www.abcr.de/shop/en/AB181158
eNovation Chemicals	D386493	http://www.enovationchem.com/productDetails.asp?productID=D386493
iChemical	EBD2126862	http://www.ichemical.com/products/59865-13-3.html?utm_source=PubChem&utm_medium=website&utm_campaign=product%20catalogs
iChemical	EBD2224706	http://www.ichemical.com/products/79217-60-0.html?utm_source=PubChem&utm_medium=website&utm_campaign=product%20catalogs

PubMed

Title	Date	PubMed
A randomized, multicenter comparison of tacrolimus and cyclosporine immunosuppressive regimens in cardiac transplantation: decreased hyperlipidemia and hypertension with tacrolimus.	1999 Apr	10226898
Acute myopathy induced by colchicine in a cyclosporine treated heart transplant recipient: possible role of the multidrug resistance transporter.	1999 Aug	10455999
Relation between long-term steroid treatment after heart transplantation, hypofibrinolysis and myocardial microthrombi generation.	1999 Jul	10452346
Cyclosporine-induced encephalopathy predisposed by diltiazem in a patient with aplastic anemia.	1999 Jun	10410193
Protective effect of cyclosporin A and FK506 from nitric oxide-dependent apoptosis in activated macrophages.	1999 Mar	10205001
Aplastic anemia responsive to cyclosporine complicating the evolution of polycythemia vera.	1999 May	10342591
Enhancement of low density lipoprotein catabolism by non-steroidal anti-inflammatory drugs in cultured HepG2 cells.	1999 May 21	10395027
Calcineurin and vacuolar-type H+-ATPase modulate macrophage effector functions.	1999 May 25	10339586
Which calcineurin inhibitor is preferred in renal transplantation: tacrolimus or cyclosporine?	1999 Nov	10630811
Cyclosporin A and imipenem associated seizure activity in allogeneic bone marrow transplantation patients.	1999 Oct	10632390
Neuronal survival activity of s100betabeta is enhanced by calcineurin inhibitors and requires activation of NF-kappaB.	1999 Sep	10463953
Arteriolopathy in non-episode biopsies of renal transplant allograft.	2000	11092348
Cyclosporin-induced flushing in a renal transplant recipient resolving after substitution with tacrolimus.	2000 Apr	10792253
Nitric oxide mediates cyclosporine-induced apoptosis in cultured renal cells.	2000 Apr	10760090
Cyclosporine withdrawal in stable renal transplant recipients after azathioprine-mycophenolate mofetil conversion.	2000 Dec	11127309
Impact of cyclosporin A pharmacokinetics on the presence of side effects in pediatric renal transplantation.	2000 Feb	10665942
Calcineurin-mediated hypertrophy protects cardiomyocytes from apoptosis in vitro and in vivo: An apoptosis-independent model of dilated heart failure.	2000 Feb 18	10679475
Cloning and expression of murine sister of P-glycoprotein reveals a more discriminating transporter than MDR1/P-glycoprotein.	2000 Jan	10617675
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	10636889
Cortical laminar necrosis caused by immunosuppressive therapy and chemotherapy.	2000 Mar	10730638
Endothelial dysfunction in renal transplant recipients maintained on cyclosporine.	2000 Mar	10720962
Ticlopidine-induced aplastic anemia: development of chromosomal abnormalities and response to immunosuppressive therapy.	2000 Mar	10679804
Immunosuppressive drugs: the first 50 years and a glance forward.	2000 May	10878284
Design of a Gag pentapeptide analogue that binds human cyclophilin A more efficiently than the entire capsid protein: new insights for the development of novel anti-HIV-1 drugs.	2000 May 4	10794694
Tacrolimus has less fibrogenic potential than cyclosporin A in a model of renal ischaemia-reperfusion injury.	2000 Nov	11091246
Calmodulin kinases II and IV and calcineurin are involved in leukemia inhibitory factor-induced cardiac hypertrophy in rats.	2000 Nov 10	11073891
Renal cholesterol accumulation: a durable response after acute and subacute renal insults.	2001 Aug	11485932
Bone marrow aplasia after pipobroman: an immune-mediated mechanism?	2001 Dec	11736962
Cyclosporin-induced hypertension.	2001 Dec	11725176
End-stage renal disease (ESRD) after orthotopic liver transplantation (OLTX) using calcineurin-based immunotherapy: risk of development and treatment.	2001 Dec 27	11773892
Replacement of calcineurin inhibitors with mycophenolate mofetil in liver-transplant patients with renal dysfunction: a randomised controlled study.	2001 Feb 24	11558484
What is proper treatment for Wegener granulomatosis?	2001 Jul 23	11485512
Fatal acute hepatic failure induced by danazol in a patient with endometriosis and aplastic anemia.	2001 Nov	11757752
Buerger's disease in a patient with minimal-change nephrotic syndrome.	2001 Nov	11598405
Cyclosporine A-induced mammary hyperplasia and hyperprolactinemia in New Zealand White rabbits.	2001 Oct	11924803
Doxorubicin ototoxicity is induced in mice by combination treatment with cyclosporin A.	2001 Oct	11718240
Sirolimus and mycophenolate mofetil for calcineurin-free immunosuppression in renal transplant recipients.	2001 Oct	11583940
Drug-associated thrombotic thrombocytopenic purpura-hemolytic uremic syndrome.	2001 Sep	11604563
Role of calcineurin in insulin-like growth factor-1-induced hypertrophy of cultured adult rat ventricular myocytes.	2001 Sep	11548882
Silencer activity of NFATc2 in the interleukin-12 receptor beta 2 proximal promoter in human T helper cells.	2001 Sep 14	11438525
Calcineurin-GATA4 pathway is involved in beta-adrenergic agonist-responsive endothelin-1 transcription in cardiac myocytes.	2001 Sep 14	11435416
Studies of renal injury IV: The GLUT1 gene protects renal cells from cyclosporine A toxicity.	2002 Jul	12081571
Dissociated ROS production and ceramide generation in sulfasalazine-induced cell death in Raw 264.7 cells.	2002 Oct	12377949
Evaluation of carcinogenic responses in the Eker rat following short-term exposure to selected nephrotoxins and carcinogens.	2002 Sep-Oct	12371664

Patents

Sample Use Guides

In Vivo Use Guide

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

In Vitro Use Guide

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.

Name

Type

Language

CYCLOSPORINE

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

Official Name

English

ciclosporin [INN]

Common Name

English

CYCLOSPORINE [USP IMPURITY]

Common Name

English

CYCLOSPORINE [USP MONOGRAPH]

Common Name

English

CYCLOSPORIN A

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