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Details

Stereochemistry ABSOLUTE
Molecular Formula C18H23N5O3.ClH
Molecular Weight 393.868
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CAFEDRINE HYDROCHLORIDE

SMILES

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

InChI

InChIKey=UTTZHZDGHMJDPM-NXCSSKFKSA-N
InChI=1S/C18H23N5O3.ClH/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;1H/t12-,15-;/m0./s1

HIDE SMILES / InChI

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

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
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
Clinical efficacy of beta1 selective adrenergic blockers in the treatment of neurocardiogenic syncope - a meta-analysis.
2010
Patents

Patents

Substance Class Chemical
Created
by admin
on Fri Dec 15 17:34:14 GMT 2023
Edited
by admin
on Fri Dec 15 17:34:14 GMT 2023
Record UNII
L0N3M64B9R
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CAFEDRINE HYDROCHLORIDE
MART.   WHO-DD  
Common Name English
7-(2-(.BETA.-HYDROXY-.ALPHA.-METHYLPHENETHYLAMINO)ETHYL)THEOPHYLLINE HYDROCHLORIDE
Systematic Name English
CAFEDRINE HYDROCHLORIDE [MART.]
Common Name English
CAFEDRINE HCL
Common 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-, MONOHYDROCHLORIDE
Common Name English
NOREPHEDRINE THEOPHYLLINE
Common Name English
Cafedrine hydrochloride [WHO-DD]
Common Name English
Code System Code Type Description
PUBCHEM
5492688
Created by admin on Fri Dec 15 17:34:14 GMT 2023 , Edited by admin on Fri Dec 15 17:34:14 GMT 2023
PRIMARY
SMS_ID
100000088420
Created by admin on Fri Dec 15 17:34:14 GMT 2023 , Edited by admin on Fri Dec 15 17:34:14 GMT 2023
PRIMARY
EVMPD
SUB00934MIG
Created by admin on Fri Dec 15 17:34:14 GMT 2023 , Edited by admin on Fri Dec 15 17:34:14 GMT 2023
PRIMARY
EPA CompTox
DTXSID20952734
Created by admin on Fri Dec 15 17:34:14 GMT 2023 , Edited by admin on Fri Dec 15 17:34:14 GMT 2023
PRIMARY
ECHA (EC/EINECS)
221-243-0
Created by admin on Fri Dec 15 17:34:14 GMT 2023 , Edited by admin on Fri Dec 15 17:34:14 GMT 2023
PRIMARY
FDA UNII
L0N3M64B9R
Created by admin on Fri Dec 15 17:34:14 GMT 2023 , Edited by admin on Fri Dec 15 17:34:14 GMT 2023
PRIMARY
CAS
3039-97-2
Created by admin on Fri Dec 15 17:34:14 GMT 2023 , Edited by admin on Fri Dec 15 17:34:14 GMT 2023
PRIMARY
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