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Merck

1158504

USP

Cyclosporine

United States Pharmacopeia (USP) Reference Standard

Synonym(s):

Cyclosporin A, Antibiotic S 7481F1, Cyclosporine

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About This Item

Empirical Formula (Hill Notation):
C62H111N11O12
CAS Number:
59865-13-3
Molecular Weight:
1202.61
UNSPSC Code:
41116107
NACRES:
NA.24
PubChem Substance ID:
329749492
MDL number:
MFCD00274558
Beilstein/REAXYS Number:
3647785

Key Documents

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Product Name

Cyclosporine, United States Pharmacopeia (USP) Reference Standard

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

SMILES string

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

InChI key

PMATZTZNYRCHOR-CGLBZJNRSA-N

grade

pharmaceutical primary standard

API family

cyclosporine

manufacturer/tradename

USP

application(s)

pharmaceutical (small molecule)

format

neat

storage temp.

−20°C

Gene Information

human ... PPIA(5478)

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Analysis Note

These products are for test and assay use only. They are not meant for administration to humans or animals and cannot be used to diagnose, treat, or cure diseases of any kind.  ​

Application

Cyclosporine USP reference standard, intended for use in specified quality tests and assays as specified in the USP compendia. Also, for use with USP monographs such as:
  • Cyclosporine Capsules
  • Cyclosporine Injection
  • Cyclosporine Oral Solution
  • Cyclosporine Compounded Ophthalmic Solution, Veterinary

Biochem/physiol Actions

A fungal metabolite possessing potent immunosuppressive properties. It inhibits the T-cell receptor signal transduction pathway via the formation of cyclosporin A−cyclophilin complex that inhibits calcineurin (protein phosphatase 2B). Inhibits nitric oxide synthesis induced by interleukin 1α, lipopolysaccharides and TNFα. Can block cytochrome c release from mitochondria.
Potent immunosuppressant; inhibits nitric oxide synthesis induced by interleukin 1α, lipopolysaccharides and TNFα; blocks cytochrome c release from mitochondria.

General description

This product is provided as delivered and specified by the issuing Pharmacopoeia. All information provided in support of this product, including SDS and any product information leaflets have been developed and issued under the Authority of the issuing Pharmacopoeia. For further information and support please go to the website of the issuing Pharmacopoeia.

Other Notes

Sales restrictions may apply.

pictograms

Health hazardExclamation mark
GHS08,GHS07

signalword

Danger

Hazard Classifications

Acute Tox. 4 Oral - Carc. 1B - Repr. 1B

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk

WGK 3

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Certificates of Analysis (COA)

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Cyclosporine Injection
United States Pharmacopeia and National Formulary
United States Pharmacopeia, 43(1), 1214-1214 (2018)
Cyclosporine Capsules
United States Pharmacopeia and National Formulary
United States Pharmacopeia, 43(1), 1213-1213 (2013)
Cyclosporine
United States Pharmacopeia and National Formulary
United States Pharmacopeia, 46(4) (2021)
Cyclosporine Oral Solution
United States Pharmacopeia and National Formulary
United States Pharmacopeia, 43(1), 1216-1216 (2013)
Cyclosporine Compounded Ophthalmic Solution, Veterinary
United States Pharmacopeia and National Formulary
United States Pharmacopeia, 40(5), 1217-1217 (2020)

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