Discuss This Drug

Sirolimus

CHEBI:CHEBI_9168

Definition

A macrolide lactam isolated from Streptomyces hygroscopicus consisting of a 29-membered ring containing 4 trans double bonds, three of which are conjugated. It is an antibiotic, immunosupressive and antineoplastic agent.

Chemical Information

Molecular Formula
C51H79NO13
Molecular Mass
914.17190
Charge
0
SMILES
[H][C@]1(CC[C@@H](O)[C@@H](C1)OC)C[C@@H](C)[C@]1([H])CC(=O)[C@H](C)\C=C(C)\[C@@H](O)[C@@H](OC)C(=O)[C@H](C)C[C@H](C)\C=C\C=C\C=C(C)\[C@H](C[C@]2([H])CC[C@@H](C)[C@@](O)(O2)C(=O)C(=O)N2CCCC[C@@]2([H])C(=O)O1)OC
InChI
InChI=1S/C51H79NO13/c1-30-16-12-11-13-17-31(2)42(61-8)28-38-21-19-36(7)51(60,65-38)48(57)49(58)52-23-15-14-18-39(52)50(59)64-43(33(4)26-37-20-22-40(53)44(27-37)62-9)29-41(54)32(3)25-35(6)46(56)47(63-10)45(55)34(5)24-30/h11-13,16-17,25,30,32-34,36-40,42-44,46-47,53,56,60H,14-15,18-24,26-29H2,1-10H3/b13-11+,16-12+,31-17+,35-25+/t30-,32-,33-,34-,36-,37+,38+,39+,40-,42+,43+,44-,46-,47+,51-/m1/s1
InChIKey
QFJCIRLUMZQUOT-HPLJOQBZSA-N

Alternative Names

  • (-)-Rapamycin
  • Antibiotic AY 22989
  • Rapamune
  • rapamycin
  • sirolimus
  • Sirolimus
  • sirolimusum
  • (3S,6R,7E,9R,10R,12R,14S,15E,17E,19E,21S,23S,26R,27R,34aS)-9,27-dihydroxy-3-{(2R)-1-[(1S,3R,4R)-4-hydroxy-3-methoxycyclohexyl]propan-2-yl}-10,21-dimethoxy-6,8,12,14,20,26-hexamethyl-9,10,12,13,14,21,22,23,24,25,26,27,32,33,34,34a-hexadecahydro-3H-23,27-epoxypyrido[2,1-c][1,4]oxazacyclohentriacontine-1,5,11,28,29(4H,6H,31H)-pentone
  • (1R,9S,12S,15R,16E,18R,19R,21R,23S,24E,26E,28E,30S,32S,35R)-1,18-dihydroxy-12-{(2S)-1-[(1S,3R,4R)-4-hydroxy-3-methoxycyclohexyl]propan-2-yl}-19,30-dimethoxy-15,17,21,23,29,35-hexamethyl-11,36-dioxa-4-azatricyclo[30.3.1.0(4,9)]hexatriaconta-16,24,26,28-tetraene-2,3,10,14,20-pentone

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

core#notation
CHEBI:9168
DRON_00010000
35302
oboInOwl#hasDbXref
Wikipedia:Rapamycin

Additional References

Wikipedia:Rapamycin

🔍 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

core#notation
CHEBI:9168
oboInOwl#hasOBONamespace
chebi_ontology
DRON_00010000
35302
oboInOwl#hasDbXref
Wikipedia:Rapamycin
oboInOwl#hasAlternativeId
CHEBI:67812
oboInOwl#id
CHEBI:9168
brand_name
HYFTOR
brand_name_base
HYFTOR
generic_name
SIrolimus
product_ndc
55500-0011
RO_0000087
http://purl.obolibrary.org/obo/CHEBI_76969
oboInOwl#inSubset
http://purl.obolibrary.org/obo/chebi#3_STAR
product_type
BULK INGREDIENT
marketing_category
BULK INGREDIENT FOR HUMAN PRESCRIPTION COMPOUNDING
listing_expiration_date
20241231
dosage_form
TABLET, SUGAR COATED
marketing_start_date
20000825
labeler_name
Nobelpharma America, LLC
spl_id
f18c1aa2-5f86-5458-e053-2995a90ab947
application_number
ANDA211040
route
INTRAVENOUS
package_ndc
55500-0011-2
package_description
1 kg in 1 CARTON (55500-0011-2)
package_marketing_start_date
25-AUG-00
rxcui
2596869
active_ingredient_strength
150 g/kg
nui
N0000175550
pharm_class_epc
mTOR Inhibitor Immunosuppressant [EPC]
pharm_class
mTOR Inhibitors [MoA]
pharm_class_pe
Decreased Immunologic Activity [PE]
pharm_class_moa
mTOR Inhibitors [MoA]
manufacturer_name
Nobelpharma America, LLC
active_ingredient_name
SIROLIMUS
unii
W36ZG6FT64
spl_set_id
19880f51-badb-4846-a02a-592a210690ab
upc
0366689347028
22-rdf-syntax-ns#type
http://www.w3.org/2002/07/owl#Class
has_treatment
http://purl.obolibrary.org/obo/DOID_0070511
chebi#has_functional_parent
http://purl.obolibrary.org/obo/CHEBI_68478
rdf-schema#domain
https://w3id.org/def/predibionto#has_side_effect32268
owl#someValuesFrom
t3862031
owl#annotatedSource
t321225