1158504

Cyclosporine

United States Pharmacopeia (USP) Reference Standard

• Synonym(s): Cyclosporin A, Antibiotic S 7481F1, Cyclosporine
• Empirical Formula (Hill Notation): C₆₂H₁₁₁N₁₁O₁₂
• CAS Number: 59865-13-3
• Molecular Weight: 1202.61
• Beilstein/REAXYS Number: 3647785
• MDL number: MFCD00274558
• UNSPSC Code: 41116107
• PubChem Substance ID: 329749492
• NACRES: NA.24

Properties

• grade: pharmaceutical primary standard
• API family: cyclosporine
• manufacturer/tradename: USP
• application(s): pharmaceutical (small molecule)
• format: neat
• storage temp.: −20°C
• 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: 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
• InChI key: PMATZTZNYRCHOR-CGLBZJNRSA-N
• Gene Information: human ... PPIA(5478)

Description

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.

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.

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.  ​

Other Notes

Sales restrictions may apply.

Safety Information

• pictograms: GHS08,GHS07
• signalword: Danger
• hcodes: H302,H350,H360FD
• pcodes: P202 - P264 - P280 - P301 + P312 - P308 + P313 - P405
• 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_germany: WGK 3