Discuss This Drug

Cyclosporine

CHEBI:CHEBI_4031

Definition

A cyclic nonribosomal peptide of eleven amino acids; an immunosuppressant drug widely used in post-allogeneic organ transplant to reduce the activity of the patient's immune system, and therefore the risk of organ rejection. Also causes reversible inhibition of immunocompetent lymphocytes in the G0- and G1-phase of the cell cycle.

Chemical Information

Molecular Formula
C62H111N11O12
Molecular Mass
1202.61120
Charge
0
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
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

Alternative Names

  • Antibiotic S 7481F1
  • ciclosporin
  • Ciclosporin
  • ciclosporina
  • ciclosporine
  • ciclosporinum
  • cyclosporin A
  • Cyclosporin A
  • Cyclosporine
  • Gengraf
  • Neoral
  • Sandimmune
  • 30-ethyl-33-[(4E)-1-hydroxy-2-methylhex-4-en-1-yl]-1,4,7,10,12,15,19,25,28-nonamethyl-6,9,18,24-tetrakis(2-methylpropyl)-3,21-bis(propan-2-yl)-1,4,7,10,13,16,19,22,25,28,31-undecaazacyclotritriacontane-2,5,8,11,14,17,20,23,26,29,32-undecone
  • 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)
  • (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)
  • 30-ethyl-33-[(4E)-1-hydroxy-2-methylhex-4-en-1-yl]-6,9,18,24-tetraisobutyl-3,21-diisopropyl-1,4,7,10,12,15,19,25,28-nonamethyl-1,4,7,10,13,16,19,22,25,28,31-undecaazacyclotritriacontane-2,5,8,11,14,17,20,23,26,29,32-undecone
  • 1,11-cyclo[L-alanyl-D-alanyl-N-methyl-L-leucyl-N-methyl-L-leucyl-N-methyl-L-valyl-(E)-(2S,3R,4R)-2-amino-3-hydroxy-N,4-dimethyloct-6-enoyl-L-2-aminobutanoyl-N-methylglycyl-N-methyl-L-leucyl-L-valyl-N-methyl-L-leucine]

Treatment Applications

Drug Classification

Important Medical Information

⚕️ This information is sourced from ChEBI (Chemical Entities of Biological Interest) database and is intended for educational purposes only.

  • Always consult with a healthcare professional before starting, stopping, or modifying any medication.
  • Side effects may vary and this list may not be comprehensive.
  • Drug interactions may occur with other medications.

Additional Identifiers

oboInOwl#hasDbXref
Wikipedia:Ciclosporin
DRON_00010000
3008
core#notation
CHEBI:4031

Additional References

Wikipedia:Ciclosporin

🔍 Click on any linked disease name to learn more about the conditions this medication is used to treat, or explore related drug classifications for more information about similar medications.

Additional Attributes

listing_expiration_date
20241231
route
OPHTHALMIC
spl_id
f18c1aa2-5f84-5458-e053-2995a90ab947
package_ndc
55500-0009-3
marketing_start_date
20190628
product_type
BULK INGREDIENT
marketing_category
EXPORT ONLY
dosage_form
CAPSULE, GELATIN COATED
labeler_name
Fujian Kerui Pharmaceutical Co., Ltd.
application_number
NDA050715
product_ndc
60505-0134
package_marketing_start_date
28-JUN-19
package_description
8 kg in 1 CARTON (55500-0009-3)
oboInOwl#hasDbXref
Wikipedia:Ciclosporin
DRON_00010000
3008
oboInOwl#hasAlternativeId
CHEBI:91802
RO_0000087
http://purl.obolibrary.org/obo/CHEBI_37153
rxcui
2055026
active_ingredient_strength
.0009 mg/mL
pharm_class_moa
Calcineurin Inhibitors [MoA]
pharm_class_epc
Calcineurin Inhibitor Immunosuppressant [EPC]
nui
N0000175458
manufacturer_name
Devatis Inc.
active_ingredient_name
9-(N-METHYL-L-ISOLEUCINE)-CYCLOSPORIN A
unii
83HN0GTJ6D
spl_set_id
c36132b2-3ec7-4c43-a25e-75cbdbe3d88d
upc
0368180214304
core#notation
CHEBI:4031
pharm_class
Calcineurin Inhibitors [MoA]
brand_name_suffix
Modified
22-rdf-syntax-ns#type
http://www.w3.org/2002/07/owl#Class
has_treatment
http://purl.obolibrary.org/obo/DOID_2592
oboInOwl#hasOBONamespace
chebi_ontology
oboInOwl#id
CHEBI:4031
generic_name
cyclosporin
brand_name
CEQUA
brand_name_base
CEQUA
oboInOwl#inSubset
http://purl.obolibrary.org/obo/chebi#3_STAR
rdf-schema#range
https://w3id.org/def/predibionto#has_drug_113307
owl#annotatedSource
t214537
owl#someValuesFrom
t3318087