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 1037		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 8307	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
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 8307	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
Rheumatoid arthritis 310 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/050715s035,050716s038lbl.pdf	Primary	Approved 8307	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
Psoriasis 83 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/050715s035,050716s038lbl.pdf	Primary	Approved 8307	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

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 1670			inhibitor 1570

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
UGT1A1 200 UGT1A4 76 UGT1A6 107 UGT2B7 145 UGT2B10 25 OATP1B1 770 OATP1B3 691 NTCP 33 BCRP 678 OATP2 4 MDR 1	UGT1A1 417 UGT1A3 421 UGT1A4 345 UGT1A6 306 UGT1A7 235 UGT1A8 282 UGT1A9 378 UGT1A10 289 UGT2B4 248 UGT2B7 387 UGT2B15 202 P-gp 1491	CYP1A1 103 CYP1A2 671 CYP2D1 2

Drug as perpetrator

Target	Modality	Activity
UGT1A6 139	inhibitor 3185 Sources: https://www.tandfonline.com/doi/full/10.3109/14756366.2010.518965 Page: -	no
UGT2B10 27	inhibitor 3185 Sources: https://www.tandfonline.com/doi/full/10.3109/14756366.2010.518965 Page: -	no
UGT2B7 156	inhibitor 3185 Sources: https://www.tandfonline.com/doi/full/10.3109/14756366.2010.518965 Page: -	no
OATP1B3 700	inhibitor 3185 Sources: https://pubmed.ncbi.nlm.nih.gov/23881596/ Page: -	yes [IC50 0.05 uM]
OATP1B1 785	inhibitor 3185 Sources: https://pubmed.ncbi.nlm.nih.gov/23881596/ Page: -	yes [IC50 0.1 uM]
OATP2 4	inhibitor 3185 Sources: https://jpet.aspetjournals.org/content/304/2/610.short Page: -	yes [IC50 0.2 uM]
BCRP 751	inhibitor 3185 Sources: https://pubmed.ncbi.nlm.nih.gov/23881596/ Page: -	yes [IC50 2 uM]
UGT1A4 79	inhibitor 3185 Sources: https://www.tandfonline.com/doi/full/10.3109/14756366.2010.518965 Page: -	yes [IC50 23 uM]
NTCP 34	inhibitor 3185 Sources: https://pubmed.ncbi.nlm.nih.gov/23881596/ Page: -	yes [IC50 4.5 uM]
UGT1A1 249	inhibitor 3185 Sources: https://www.tandfonline.com/doi/full/10.3109/14756366.2010.518965 Page: -	yes [IC50 48 uM]
CYP1A1 206	inducer 1515 Sources: https://pubmed.ncbi.nlm.nih.gov/8361996/ Page: -	yes
CYP1A2 1620	inducer 1515 Sources: https://pubmed.ncbi.nlm.nih.gov/8361996/ Page: -	yes
CYP2D1 8	inducer 1515 Sources: https://pubmed.ncbi.nlm.nih.gov/8361996/ Page: -	yes
MDR 1	inhibitor 3185 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 387	substrate 3264 Sources: https://www.sciencedirect.com/science/article/pii/S016882780100040X Page: -	major
UGT1A1 417	substrate 3264 Sources: https://www.sciencedirect.com/science/article/pii/S016882780100040X Page: -	minor
UGT1A10 289	substrate 3264 Sources: https://www.sciencedirect.com/science/article/pii/S016882780100040X Page: -	minor
UGT1A3 421	substrate 3264 Sources: https://www.sciencedirect.com/science/article/pii/S016882780100040X Page: -	minor
UGT1A4 345	substrate 3264 Sources: https://www.sciencedirect.com/science/article/pii/S016882780100040X Page: -	no
UGT1A6 306	substrate 3264 Sources: https://www.sciencedirect.com/science/article/pii/S016882780100040X Page: -	no
UGT1A7 235	substrate 3264 Sources: https://www.sciencedirect.com/science/article/pii/S016882780100040X Page: -	no
UGT1A8 282	substrate 3264 Sources: https://www.sciencedirect.com/science/article/pii/S016882780100040X Page: -	no
UGT1A9 378	substrate 3264 Sources: https://www.sciencedirect.com/science/article/pii/S016882780100040X Page: -	no
UGT2B15 202	substrate 3264 Sources: https://www.sciencedirect.com/science/article/pii/S016882780100040X Page: -	no
UGT2B4 248	substrate 3264 Sources: https://www.sciencedirect.com/science/article/pii/S016882780100040X Page: -	no
CYP3A4 1670	substrate 3264 Sources: https://link.springer.com/article/10.1007%2FBF03190040 Page: -	yes
P-gp 1491	substrate 3264 Sources: https://www.sciencedirect.com/science/article/pii/S0085253815520577 Page: -	yes

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 1603	inhibitor 1584 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
Nephrotoxicity after orthotopic liver transplantation in cyclosporin A and FK 506-treated patients.	1994	11271297
Neurotoxicity after orthotopic liver transplantation in cyclosporin A- and FK 506-treated patients.	1994	11271254
Rotenone and pyruvate prevent the tert-butylhydroperoxide-induced necrosis of U937 cells and allow them to proliferate.	1999 Aug 20	10486581
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
Neuronal survival activity of s100betabeta is enhanced by calcineurin inhibitors and requires activation of NF-kappaB.	1999 Sep	10463953
Hemolytic-uremic syndrome in association with both cyclosporine and tacrolimus.	2000	11140243
Nitric oxide mediates cyclosporine-induced apoptosis in cultured renal cells.	2000 Apr	10760090
Inhibitory effect of human immunodeficiency virus protease inhibitors on multidrug resistance transporter P-glycoproteins.	2000 Dec	11145192
Comparison of enalapril and valsartan in cyclosporine A-induced hypertension and nephrotoxicity in spontaneously hypertensive rats on high-sodium diet.	2000 Jul	10903974
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
Calmodulin kinases II and IV and calcineurin are involved in leukemia inhibitory factor-induced cardiac hypertrophy in rats.	2000 Nov 10	11073891
[Arterial hypertension and oxidative stress induced by cyclosporin. Effect of carvedilol].	2001 Apr-Jun	11688356
Replacement of calcineurin inhibitors with mycophenolate mofetil in liver-transplant patients with renal dysfunction: a randomised controlled study.	2001 Feb 24	11558484
Cyclosporine A-induced mammary hyperplasia and hyperprolactinemia in New Zealand White rabbits.	2001 Oct	11924803
Use of rapamycin in a transplant patient who developed cyclosporin neurotoxicity.	2001 Oct	11605780
Vascular endothelial function in cyclosporine and tacrolimus treated renal transplant recipients.	2001 Oct 27	11685108
Alterations induced by cyclosporine A in myocardial fibers and extracellular matrix in rat.	2002	12168785
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
Colchicine myoneuropathy in a renal transplant patient.	2002 Jul	12122515
Nephrotoxicity of cyclosporine A and amphotericin B-deoxycholate as continuous infusion in allogenic stem cell transplantation.	2002 Jun 15	12362282

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 16 18:25:55 UTC 2022` Edited by `admin` on `Fri Dec 16 18:25:55 UTC 2022`
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

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