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

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

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
[Arterial hypertension and oxidative stress induced by cyclosporin. Effect of carvedilol].	2001 Apr-Jun	11688356
Renal cholesterol accumulation: a durable response after acute and subacute renal insults.	2001 Aug	11485932
Calcineurin-inhibitor related nephrotoxicity- reversibility in paediatric liver transplant recipients.	2001 Aug 27	11544444
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
Mycophenolate mofetil monotherapy in liver transplantation.	2001 Feb 24	11558493
Replacement of calcineurin inhibitors with mycophenolate mofetil in liver-transplant patients with renal dysfunction: a randomised controlled study.	2001 Feb 24	11558484
Cyclosporin A for the treatment of patients with chronic idiopathic thrombocytopenic purpura refractory to corticosteroids or splenectomy.	2001 Jul	11472356
What is proper treatment for Wegener granulomatosis?	2001 Jul 23	11485512
Functional characterization of the human multidrug transporter, ABCG2, expressed in insect cells.	2001 Jul 6	11437380
Fatal acute hepatic failure induced by danazol in a patient with endometriosis and aplastic anemia.	2001 Nov	11757752
Targeting keratinocyte apoptosis in the treatment of atopic dermatitis and allergic contact dermatitis.	2001 Nov	11692113
Buerger's disease in a patient with minimal-change nephrotic syndrome.	2001 Nov	11598405
Severe neurotoxicity of tacrolimus (FK506) after renal transplantation: two case reports.	2001 Nov-Dec	11750573
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
Cyclosporin A-induced encephalopathy after allogeneic bone marrow transplantation with prevention of graft-versus-host disease by tacrolimus.	2001 Oct	11704797
Use of rapamycin in a transplant patient who developed cyclosporin neurotoxicity.	2001 Oct	11605780
Sirolimus and mycophenolate mofetil for calcineurin-free immunosuppression in renal transplant recipients.	2001 Oct	11583940
Changes in lipid metabolism and effect of simvastatin in renal transplant recipients induced by cyclosporine or tacrolimus.	2001 Oct	11583721
Correlates of acute renal failure in patients receiving parenteral amphotericin B.	2001 Oct	11576359
Vascular endothelial function in cyclosporine and tacrolimus treated renal transplant recipients.	2001 Oct 27	11685108
Drug-associated thrombotic thrombocytopenic purpura-hemolytic uremic syndrome.	2001 Sep	11604563
Cholestasis and regulation of genes related to drug metabolism and biliary transport in rat liver following treatment with cyclosporine A and sirolimus (Rapamycin).	2001 Sep	11589784
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
Alterations induced by cyclosporine A in myocardial fibers and extracellular matrix in rat.	2002	12168785
Oxidative stress and TGFbeta in kidney-transplanted patients with cyclosporin-induced hypertension. Effect of carvedilol and nifedipine.	2002 Aug	12227681
Angiotensin II regulation of vascular endothelial growth factor and receptors Flt-1 and KDR/Flk-1 in cyclosporine nephrotoxicity.	2002 Aug	12110003
Myelodysplastic syndrome complicated by autoimmune hemolytic anemia: remission of refractory anemia following mycophenolate mofetil.	2002 Dec	12483369
Sirolimus: new preparation. No tangible advance in renal transplantation.	2002 Dec	12469693
Expression of TGF-beta and fibrogenic genes in transplant recipients with tacrolimus and cyclosporine nephrotoxicity.	2002 Dec	12427154
Cyclosporine-associated facial paralysis in a child with renal transplant.	2002 Jul	12172772
Colchicine myoneuropathy in a renal transplant patient.	2002 Jul	12122515
Studies of renal injury IV: The GLUT1 gene protects renal cells from cyclosporine A toxicity.	2002 Jul	12081571
Calcineurin inhibitors, cyclosporin A and tacrolimus inhibit expression of inducible nitric oxide synthase in colon epithelial and macrophage cell lines.	2002 Jul 19	12144947
Dermatomyositis associated with membranous nephropathy in a 43-year-old female.	2002 Jul-Aug	12169874
Nephrotoxicity of cyclosporine A and amphotericin B-deoxycholate as continuous infusion in allogenic stem cell transplantation.	2002 Jun 15	12362282
Itraconazole-induced rhabdomyolysis and acute renal failure in a heart transplant recipient treated with simvastatin and cyclosporine.	2002 Jun 27	12131698
Enhancement by cyclosporin A of taxol-induced apoptosis of human urinary bladder cancer cells.	2002 May	12086014
Sirolimus (Rapamune) in renal transplantation.	2002 Nov	12394605
Dissociated ROS production and ceramide generation in sulfasalazine-induced cell death in Raw 264.7 cells.	2002 Oct	12377949
Oxidative stress in kidney transplant patients with calcineurin inhibitor-induced hypertension: effect of ramipril.	2002 Oct	12352326
Pimecrolimus inhibits up-regulation of OX40 and synthesis of inflammatory cytokines upon secondary T cell activation by allogeneic dendritic cells.	2002 Oct	12296857
Interaction of cytochrome P450 3A inhibitors with P-glycoprotein.	2002 Oct	12235267
Long-term comparison of tacrolimus- and cyclosporine-induced nephrotoxicity in pediatric heart-transplant recipients.	2002 Sep	12243498
Influence of different chemicals on MDR-1 P-glycoprotein expression and activity in the HK-2 proximal tubular cell line.	2002 Sep 1	12387747
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.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:51:52 GMT 2023` Edited by `admin` on `Fri Dec 15 15:51:52 GMT 2023`
Record UNII	83HN0GTJ6D
Record Status	`Validated (UNII)`
Record Version

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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