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Details

Stereochemistry ABSOLUTE
Molecular Formula C18H23N5O3
Molecular Weight 357.4069
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CAFEDRINE

SMILES

C[C@H](NCCN1C=NC2=C1C(=O)N(C)C(=O)N2C)[C@H](O)C3=CC=CC=C3

InChI

InChIKey=UJSKUDDDPKGBJY-WFASDCNBSA-N
InChI=1S/C18H23N5O3/c1-12(15(24)13-7-5-4-6-8-13)19-9-10-23-11-20-16-14(23)17(25)22(3)18(26)21(16)2/h4-8,11-12,15,19,24H,9-10H2,1-3H3/t12-,15-/m0/s1

HIDE SMILES / InChI

Molecular Formula C18H23N5O3
Molecular Weight 357.4069
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Cafedrine, also known as norephedrinoethyltheophylline, is a chemical linkage of norephedrine and theophylline and is a cardiac stimulant used to increase blood pressure in people with hypotension. There are few data available for cafedrine. Cafedrine has a half-life of 60 min following both oral and intravenous administration Cafedrine is metabolized to norephedrine and several minor metabolites, but nearly 90% of the administered norephedrine is excreted via the kidneys, mostly unchanged, within 24 h. The effects of cafedrine on cardiac output are believed to be mediated via β- adrenoceptors. Cafedrine has a positive inotropic effect in humans, and this can be abolished by administration of the non-selective β-adrenoceptor antagonist propranolol. A combination of cafedrine and theodrenaline called Akrinor® is used for the treatment of hypotension in adults that occurs during emergency situations, general anesthesia, and regional anesthesia, especially during cesarean sections. Cafedrine/theodrenaline may have advantages over other vasopressor drugs. For example, it can be administered via bolus while catecholamines normally need to be diluted and administered via syringe pumps. Bolus injection is faster, which may be beneficial in emergency situations, plus it is more cost efficient with respect to the disposables. Cafedrine/theodrenaline has been widely used in Germany since 1963

Approval Year

PubMed

PubMed

TitleDatePubMed
[Spinal anesthesia for cesarean section].
2001 Jan
[Mydriasis not reacting to light during an uneventful esophagectomy--drug-related side effect of Akrinor?].
2003 Mar
Anesthetic management of a patient with histiocytosis X and pulmonary complications during Caesarean section.
2004 Nov
How to distinguish between ischemic and nonischemic postsystolic thickening: a strain rate imaging study.
2006 Jan
[Ephedrine as alternative to Akrinor in regional obstetric anesthesia].
2006 Jul
[Old drugs and new approval procedures: Akrinor remains marketable and an application for reapproval of Arginin Vasopressin has been made].
2006 Jun
Akrinor-induced relaxation of pig coronary artery in vitro is transformed into alpha1-adrenoreceptor-mediated contraction by pretreatment with propranolol.
2006 Mar
[Preoperative administration of angiotensin-converting enzyme inhibitors].
2007 Jun
Glioblastoma cells express functional cell membrane receptors activated by daily used medical drugs.
2009 Dec
Clinical efficacy of beta1 selective adrenergic blockers in the treatment of neurocardiogenic syncope - a meta-analysis.
2010
Impact of cafedrine/theodrenaline (Akrinor® ) on therapy of maternal hypotension during spinal anesthesia for Cesarean delivery: a retrospective study.
2010 Dec
Patents

Patents

Substance Class Chemical
Created
by admin
on Fri Dec 15 16:39:12 GMT 2023
Edited
by admin
on Fri Dec 15 16:39:12 GMT 2023
Record UNII
0UYY5V4U2Q
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CAFEDRINE
INN   WHO-DD  
INN  
Official Name English
cafedrine [INN]
Common Name English
(-)-CAFEDRINE
Common Name English
7-(2-(2-HYDROXY-1-METHYLPHENETHYLAMINO)ETHYL)THEOPHYLLINE
Systematic Name English
1H-PURINE-2,6-DIONE, 3,7-DIHYDRO-7-(2-(((1S,2R)-2-HYDROXY-1-METHYL-2-PHENYLETHYL)AMINO)ETHYL)-1,3-DIMETHYL-
Systematic Name English
NOREPHENDRINETHEOPHYLLINE
Common Name English
7-(2-(.BETA.-HYDROXY-.ALPHA.-METHYLPHENETHYLAMINO)ETHYL)THEOPHYLLINE
Systematic Name English
Cafedrine [WHO-DD]
Common Name English
Classification Tree Code System Code
WHO-VATC QC01CA21
Created by admin on Fri Dec 15 16:39:12 GMT 2023 , Edited by admin on Fri Dec 15 16:39:12 GMT 2023
NCI_THESAURUS C47795
Created by admin on Fri Dec 15 16:39:12 GMT 2023 , Edited by admin on Fri Dec 15 16:39:12 GMT 2023
WHO-ATC C01CA21
Created by admin on Fri Dec 15 16:39:12 GMT 2023 , Edited by admin on Fri Dec 15 16:39:12 GMT 2023
Code System Code Type Description
NCI_THESAURUS
C76026
Created by admin on Fri Dec 15 16:39:12 GMT 2023 , Edited by admin on Fri Dec 15 16:39:12 GMT 2023
PRIMARY
WIKIPEDIA
Cafedrine
Created by admin on Fri Dec 15 16:39:12 GMT 2023 , Edited by admin on Fri Dec 15 16:39:12 GMT 2023
PRIMARY
INN
1668
Created by admin on Fri Dec 15 16:39:12 GMT 2023 , Edited by admin on Fri Dec 15 16:39:12 GMT 2023
PRIMARY
SMS_ID
100000081571
Created by admin on Fri Dec 15 16:39:12 GMT 2023 , Edited by admin on Fri Dec 15 16:39:12 GMT 2023
PRIMARY
DRUG BANK
DB12926
Created by admin on Fri Dec 15 16:39:12 GMT 2023 , Edited by admin on Fri Dec 15 16:39:12 GMT 2023
PRIMARY
CAS
58166-83-9
Created by admin on Fri Dec 15 16:39:12 GMT 2023 , Edited by admin on Fri Dec 15 16:39:12 GMT 2023
PRIMARY
DRUG CENTRAL
462
Created by admin on Fri Dec 15 16:39:12 GMT 2023 , Edited by admin on Fri Dec 15 16:39:12 GMT 2023
PRIMARY
FDA UNII
0UYY5V4U2Q
Created by admin on Fri Dec 15 16:39:12 GMT 2023 , Edited by admin on Fri Dec 15 16:39:12 GMT 2023
PRIMARY
EPA CompTox
DTXSID50866678
Created by admin on Fri Dec 15 16:39:12 GMT 2023 , Edited by admin on Fri Dec 15 16:39:12 GMT 2023
PRIMARY
EVMPD
SUB06044MIG
Created by admin on Fri Dec 15 16:39:12 GMT 2023 , Edited by admin on Fri Dec 15 16:39:12 GMT 2023
PRIMARY
RXCUI
47589
Created by admin on Fri Dec 15 16:39:12 GMT 2023 , Edited by admin on Fri Dec 15 16:39:12 GMT 2023
PRIMARY RxNorm
MESH
C002749
Created by admin on Fri Dec 15 16:39:12 GMT 2023 , Edited by admin on Fri Dec 15 16:39:12 GMT 2023
PRIMARY
ChEMBL
CHEMBL2104207
Created by admin on Fri Dec 15 16:39:12 GMT 2023 , Edited by admin on Fri Dec 15 16:39:12 GMT 2023
PRIMARY
PUBCHEM
5489638
Created by admin on Fri Dec 15 16:39:12 GMT 2023 , Edited by admin on Fri Dec 15 16:39:12 GMT 2023
PRIMARY
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