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Substance Name: Cyclosporine [USAN:USP]
RN: 59865-13-3
UNII: 83HN0GTJ6D
InChIKey: PMATZTZNYRCHOR-CGLBZJNRSA-N
Notes
- A cyclic undecapeptide from an extract of soil fungi. It is a powerful immunosupressant with a specific action on T-lymphocytes. It is used for the prophylaxis of graft rejection in organ and tissue transplantation. (From Martindale, The Extra Pharmacopoeia, 30th ed).
- One of the metabolites produced by Fusarium sp. S-435.
Molecular Formula
- C62-H111-N11-O12
Molecular Weight
- 1202.6239
- All
- Classifications
- Links to Resources
- Names & Synonyms
- Registry Numbers
- Structure Descriptors
- Toxicity
- Physical Properties
Classification Codes
Classification Codes
- Anti-Infective Agents
- Antifungal Agents
- Antirheumatic Agents
- Antiviral (COVID-19)
- Calcineurin Inhibitors
- Dermatologic Agents
- Drug / Therapeutic Agent
- Enzyme Inhibitors
- Human Data
- Immunologic Factors
- Immunosuppressant
- Immunosuppressive Agents
- Mutation Data
- Reproductive Effect
- Tumor Data
Superlist Classification Codes
- Known to be a Carcinogen
- Overall Carcinogenic Evaluation: Group 1
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Links to Resources
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Regulatory Agencies (Superlist Locators)
Other Resources (Internet Locators)
Search for this InChIKey on the Web
Names and Synonyms
Name of Substance
- Ciclosporin [INN]
- Cyclosporin A
- Cyclosporine [USAN:USP]
- Ramihyphin A
MeSH Heading
- Cyclosporine
Synonyms
- (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)
- 27-400
- Abrammune
- Antibiotic S 7481F1
- Arpimune ME
- CCRIS 1590
- Cicloral
- Cicloral (antibiotic)
- Ciclosporin
- Ciclosporina
- Ciclosporina Germed
- Ciclosporina [INN-Spanish]
- Ciclosporine
- Ciclosporine [INN-French]
- Ciclosporinum
- Ciclosporinum [INN-Latin]
- Cipol N
- Consupren
- 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)
- Cyclo(L-alanyl-D-alanyl-N-methyl-L-leucyl-N-methyl-L-leucyl-N-methyl-L-valyl-((3R,4R,6E)-6,7-didehydro-3-hydroxy-N,4-dimethyl-L-2-aminooctanoyl-L-2-aminobutanoyl-N-methylglycyl-N-methyl-L-leucyl-L-valyl-N-methylleucyl)
- Cyclosporin
- Cyclosporin A
- Cyclosporine
- Cyclosporine A
- Debio088
- DRG-0275
- Equoral
- Gengraf
- HSDB 6881
- Imusporin
- Neoplanta
- Neoral
- NSC 290193
- OL 27-400
- Optimmune
- Papilock Mini
- Ramihyphin A
- Restasis
- S 7481F1
- S-Neoral
- Sandimmun
- Sandimmun Neoral
- Sandimmune
- Sandimmune Neoral
- Sang 35
- Sang-35
- Sangcya
- SDZ-OXL 400
- Seciera
- Sigmasporin Microoral
- UNII-83HN0GTJ6D
- Zinograf ME
Systematic Names
- Cyclosporin A
- Cyclosporine
Superlist Names
- Ciclosporin
- Cyclosporin A
- Cyclosporine
Registry Numbers
CAS Registry Number
- 59865-13-3
FDA UNII
- 83HN0GTJ6D
Other Registry Numbers
- 104250-72-8
- 223528-56-1
- 55126-45-9
- 56645-58-0
System Generated Number
- 0059865133
Structure Descriptors
InChI
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/s1InChIKey
PMATZTZNYRCHOR-CGLBZJNRSA-NSmiles
CC[C@@H]1NC(=O)Toxicity
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
human | TDLo | oral | 12mg/kg (12mg/kg) | ENDOCRINE: ANTIDIURESIS VASCULAR: BP ELEVATION NOT CHARACTERIZED IN AUTONOMIC SECTION | Journal of Hypertension. Vol. 11, Pg. 1209, 1993. |
man | TDLo | oral | 14286ug/kg (14.286mg/kg) | BEHAVIORAL: TREMOR BEHAVIORAL: EXCITEMENT CARDIAC: ARRHYTHMIAS (INCLUDING CHANGES IN CONDUCTION) | Annals of Pharmacotherpy. Vol. 34, Pg. 405, 2000. |
man | TDLo | oral | 20mg/kg/2D-I (20mg/kg) | LUNGS, THORAX, OR RESPIRATION: CYANOSIS VASCULAR: ACUTE ARTERIAL OCCLUSION BEHAVIORAL: HEADACHE | Lancet. Vol. 2, Pg. 1092, 1986. |
man | TDLo | parenteral | 20mg/kg/5D-I (20mg/kg) | SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE SENSE ORGANS AND SPECIAL SENSES: DIPLOPIA: EYE SENSE ORGANS AND SPECIAL SENSES: VISUAL FIELD CHANGES: EYE | American Journal of Ophthalmology. Vol. 126, Pg. 607, 1998. |
man | TDLo | unreported | 30mg/kg/4D-I (30mg/kg) | KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)" | Annals of Internal Medicine. Vol. 107, Pg. 786, 1987. |
mouse | LD50 | intravenous | 96mg/kg (96mg/kg) | Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 17, Pg. 365, 1986. | |
mouse | LD50 | oral | 2329mg/kg (2329mg/kg) | BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY) SKIN AND APPENDAGES (SKIN): HAIR: OTHER GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" | Archives of Toxicology. Vol. 53, Pg. 107, 1983. |
rabbit | LD50 | intravenous | 10mg/kg (10mg/kg) | Toxicologic Pathology. Vol. 14, Pg. 73, 1986. | |
rabbit | LD50 | oral | > 1gm/kg (1000mg/kg) | GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" SKIN AND APPENDAGES (SKIN): HAIR: OTHER BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY) | Archives of Toxicology. Vol. 53, Pg. 107, 1983. |
rat | LD50 | intraperitoneal | 147mg/kg (147mg/kg) | Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 17, Pg. 365, 1986. | |
rat | LD50 | intravenous | 24mg/kg (24mg/kg) | Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 17, Pg. 365, 1986. | |
rat | LD50 | oral | 1480mg/kg (1480mg/kg) | SKIN AND APPENDAGES (SKIN): HAIR: OTHER GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY) | Archives of Toxicology. Vol. 53, Pg. 107, 1983. |
rat | LD50 | subcutaneous | 286mg/kg (286mg/kg) | Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 17, Pg. 365, 1986. | |
women | TDLo | oral | 62500ug/kg/5D (62.5mg/kg) | KIDNEY, URETER, AND BLADDER: OTHER CHANGES | Lancet. Vol. 1, Pg. 1221, 1986. |
women | TDLo | oral | 1911mg/kg/91W (1911mg/kg) | KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)" BEHAVIORAL: COMA BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD | British Journal of Rheumatology. Vol. 33, Pg. 90, 1994. |
Physical Properties
Physical Property | Value | Units | Temp (deg C) | Source |
---|---|---|---|---|
Melting Point | 148-151 | deg C | EXP | |
log P (octanol-water) | 2.92 | (none) | EXP | |
Atmospheric OH Rate Constant | 3.46E-10 | cm3/molecule-sec | 25 | EST |
Physical property data is provided to ChemIDplus by SRC, Inc.