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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
 

Classification Codes

Classification Codes

  • Anti-Infective Agents
  • Antifungal Agents
  • Antirheumatic Agents
  • 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

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/s1

InChIKey

PMATZTZNYRCHOR-CGLBZJNRSA-N

Smiles

CC[C@@H]1NC(=O)[C@H]([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)C1=O)C(C)C

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.