U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C15H23NO2.ClH
Molecular Weight 285.81
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CIRAMADOL HYDROCHLORIDE

SMILES

Cl.[H][C@@]1(CCCC[C@H]1O)[C@@H](N(C)C)C2=CC=CC(O)=C2

InChI

InChIKey=XBNIHQOJYIOGEU-HWKASLJMSA-N
InChI=1S/C15H23NO2.ClH/c1-16(2)15(11-6-5-7-12(17)10-11)13-8-3-4-9-14(13)18;/h5-7,10,13-15,17-18H,3-4,8-9H2,1-2H3;1H/t13-,14+,15-;/m0./s1

HIDE SMILES / InChI

Molecular Formula C15H23NO2
Molecular Weight 249.3486
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 3 / 3
E/Z Centers 0
Optical Activity UNSPECIFIED

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Ciramadol is an opioid agonist-antagonist analgesic with low potential for dependency. Ciramadol appears to be an effective analgesic, with tolerable gastrointestinal central nervous system side effects at both the 30-and 90-mg dose levels. Ciramadol is a mixed agonist-antagonist for the μ-opioid receptor. Side effects might include nausea and vomiting.

Approval Year

PubMed

PubMed

TitleDatePubMed
Patents

Sample Use Guides

In Vivo Use Guide
Curator's Comment: Intramuscular route is also possible: Efficacy and safety of the analgesic ciramadol in the management of postoperative pain was evaluated in 139 healthy patients given single, double-blind, intramuscular injections of either 30 mg ciramadol, 60 mg ciramadol, 10 mg morphine or 0.9% saline on the first or second postoperative day. During the first hour after administration, some measurements showed that 30 mg ciramadol was superior to 60 mg ciramadol. https://www.ncbi.nlm.nih.gov/pubmed/6348105
Ciramadol was compared in 30 and 60 mg doses with pentazocine 50 mg, aspirin 650 mg, and placebo in the treatment of 153 patients with postoperative pain. All drugs were administered between six and 72 hours after surgery. Analgesic efficacy was assessed for six hours after study drug administration using verbal pain intensity, analog pain intensity, and verbal pain relief scales. Significantly higher analgesic efficacy scores were seen with ciramadol 30 mg than with pentazocine 50 mg and placebo at most of the evaluation points. Doses of ciramadol 30 mg were significantly more effective than aspirin 650 mg at several time periods, and ciramadol 60 mg was better than pentazocine and placebo at several evaluation times. The 30-mg dose of ciramadol was generally more effective than the 60-mg dose.
Route of Administration: Oral
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:11:54 GMT 2023
Edited
by admin
on Fri Dec 15 15:11:54 GMT 2023
Record UNII
090XO8449J
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CIRAMADOL HYDROCHLORIDE
MI   USAN  
USAN  
Official Name English
PHENOL, 3-((DIMETHYLAMINO)(2-HYDROXYCYCLOHEXYL)METHYL)-, HYDROCHLORIDE, (1R-(1.ALPHA.(R*),2.ALPHA.))- (-)-
Common Name English
CIRAMADOL HYDROCHLORIDE [USAN]
Common Name English
WY-15705 HYDROCHLORIDE
Code English
WY-15,705 HYDROCHLORIDE
Code English
CIRAMADOL HCL
Common Name English
CIRAMADOL HYDROCHLORIDE [MI]
Common Name English
CIRADOL
Brand Name English
WY-15,705 HCL
Code English
(-)-(1R,2R)-2-((R)-.ALPHA.-(DIMETHYLAMINO)-M-HYDROXYBENZYL)CYCLOHEXANOL HYDROCHLORIDE
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C67413
Created by admin on Fri Dec 15 15:11:54 GMT 2023 , Edited by admin on Fri Dec 15 15:11:54 GMT 2023
NCI_THESAURUS C1506
Created by admin on Fri Dec 15 15:11:54 GMT 2023 , Edited by admin on Fri Dec 15 15:11:54 GMT 2023
Code System Code Type Description
NCI_THESAURUS
C65334
Created by admin on Fri Dec 15 15:11:54 GMT 2023 , Edited by admin on Fri Dec 15 15:11:54 GMT 2023
PRIMARY
EPA CompTox
DTXSID40979443
Created by admin on Fri Dec 15 15:11:54 GMT 2023 , Edited by admin on Fri Dec 15 15:11:54 GMT 2023
PRIMARY
USAN
W-77
Created by admin on Fri Dec 15 15:11:54 GMT 2023 , Edited by admin on Fri Dec 15 15:11:54 GMT 2023
PRIMARY
CAS
63323-46-6
Created by admin on Fri Dec 15 15:11:54 GMT 2023 , Edited by admin on Fri Dec 15 15:11:54 GMT 2023
PRIMARY
ECHA (EC/EINECS)
264-099-4
Created by admin on Fri Dec 15 15:11:54 GMT 2023 , Edited by admin on Fri Dec 15 15:11:54 GMT 2023
PRIMARY
MERCK INDEX
m653
Created by admin on Fri Dec 15 15:11:54 GMT 2023 , Edited by admin on Fri Dec 15 15:11:54 GMT 2023
PRIMARY Merck Index
MESH
C018273
Created by admin on Fri Dec 15 15:11:54 GMT 2023 , Edited by admin on Fri Dec 15 15:11:54 GMT 2023
PRIMARY
ChEMBL
CHEMBL2104132
Created by admin on Fri Dec 15 15:11:54 GMT 2023 , Edited by admin on Fri Dec 15 15:11:54 GMT 2023
PRIMARY
FDA UNII
090XO8449J
Created by admin on Fri Dec 15 15:11:54 GMT 2023 , Edited by admin on Fri Dec 15 15:11:54 GMT 2023
PRIMARY
PUBCHEM
44462
Created by admin on Fri Dec 15 15:11:54 GMT 2023 , Edited by admin on Fri Dec 15 15:11:54 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY