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Details

Stereochemistry ABSOLUTE
Molecular Formula C15H23NO2
Molecular Weight 249.3486
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CIRAMADOL

SMILES

CN(C)[C@H]([C@H]1CCCC[C@H]1O)C2=CC(O)=CC=C2

InChI

InChIKey=UVTLONZTPXCUPU-ZNMIVQPWSA-N
InChI=1S/C15H23NO2/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/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

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
Comparative evaluation of morphine, pentazocine and ciramadol in postaddicts.
1987-03
Inhibition of ciramadol glucuronidation by benzodiazepines.
1986-07-01
Oral ciramadol: a new analgesic for postoperative pain.
1986-02
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 Wed Apr 02 08:20:59 GMT 2025
Edited
by admin
on Wed Apr 02 08:20:59 GMT 2025
Record UNII
9NQ109OW0G
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
WY-15,705
Preferred Name English
CIRAMADOL
INN   MART.   MI   USAN  
INN   USAN  
Official Name English
ciramadol [INN]
Common Name English
CIRAMADOL [MART.]
Common Name English
CIRAMADOL [USAN]
Common Name English
(-)-(1R,2R)-2-((R)-.ALPHA.-(DIMETHYLAMINO)-M-HYDROXYBENZYL)CYCLOHEXANOL
Systematic Name English
CIRAMADOL [MI]
Common Name English
PHENOL, 3-((DIMETHYLAMINO)(2-HYDROXYCYCLOHEXYL)METHYL)-, (1R-(1.ALPHA.(R*),2.ALPHA.))-(-)-
Common Name English
WY-15705
Code English
Classification Tree Code System Code
NCI_THESAURUS C67413
Created by admin on Wed Apr 02 08:20:59 GMT 2025 , Edited by admin on Wed Apr 02 08:20:59 GMT 2025
Code System Code Type Description
MERCK INDEX
m653
Created by admin on Wed Apr 02 08:20:59 GMT 2025 , Edited by admin on Wed Apr 02 08:20:59 GMT 2025
PRIMARY Merck Index
ChEMBL
CHEMBL2104132
Created by admin on Wed Apr 02 08:20:59 GMT 2025 , Edited by admin on Wed Apr 02 08:20:59 GMT 2025
PRIMARY
FDA UNII
9NQ109OW0G
Created by admin on Wed Apr 02 08:20:59 GMT 2025 , Edited by admin on Wed Apr 02 08:20:59 GMT 2025
PRIMARY
INN
4464
Created by admin on Wed Apr 02 08:20:59 GMT 2025 , Edited by admin on Wed Apr 02 08:20:59 GMT 2025
PRIMARY
PUBCHEM
44463
Created by admin on Wed Apr 02 08:20:59 GMT 2025 , Edited by admin on Wed Apr 02 08:20:59 GMT 2025
PRIMARY
WIKIPEDIA
Ciramadol
Created by admin on Wed Apr 02 08:20:59 GMT 2025 , Edited by admin on Wed Apr 02 08:20:59 GMT 2025
PRIMARY
EVMPD
SUB07477MIG
Created by admin on Wed Apr 02 08:20:59 GMT 2025 , Edited by admin on Wed Apr 02 08:20:59 GMT 2025
PRIMARY
EPA CompTox
DTXSID601018412
Created by admin on Wed Apr 02 08:20:59 GMT 2025 , Edited by admin on Wed Apr 02 08:20:59 GMT 2025
PRIMARY
DRUG CENTRAL
3713
Created by admin on Wed Apr 02 08:20:59 GMT 2025 , Edited by admin on Wed Apr 02 08:20:59 GMT 2025
PRIMARY
NCI_THESAURUS
C77282
Created by admin on Wed Apr 02 08:20:59 GMT 2025 , Edited by admin on Wed Apr 02 08:20:59 GMT 2025
PRIMARY
CAS
63269-31-8
Created by admin on Wed Apr 02 08:20:59 GMT 2025 , Edited by admin on Wed Apr 02 08:20:59 GMT 2025
PRIMARY
SMS_ID
100000081524
Created by admin on Wed Apr 02 08:20:59 GMT 2025 , Edited by admin on Wed Apr 02 08:20:59 GMT 2025
PRIMARY
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