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Details

Stereochemistry RACEMIC
Molecular Formula C12H21N5O3
Molecular Weight 283.3268
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CADRALAZINE

SMILES

CCOC(=O)NNC1=NN=C(C=C1)N(CC)CC(C)O

InChI

InChIKey=QLTVVOATEHFXLT-UHFFFAOYSA-N
InChI=1S/C12H21N5O3/c1-4-17(8-9(3)18)11-7-6-10(13-15-11)14-16-12(19)20-5-2/h6-7,9,18H,4-5,8H2,1-3H3,(H,13,14)(H,16,19)

HIDE SMILES / InChI

Molecular Formula C12H21N5O3
Molecular Weight 283.3268
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Cadralazine is an antihypertensive of the hydrazinophthalazine chemical class. In hypertensive patients the optimal effect, based on the antihypertensive efficacy to tolerability ratio, is seen after a 15 mg dose when the drug is administered as monotherapy. When administered in combination with other antihypertensive agents, a 10 mg daily dosage seems appropriate. Noncomparative trials have shown that, in patients who had failed to respond adequately to a beta-blocker and/or diuretic, the addition of cadralazine 10 to 30 mg once daily reduced systolic/diastolic blood pressure by 11 to 19%/13 to 22%. This antihypertensive effect becomes evident over a 2- to 6-week period of therapy and persists during longer term administration. Comparative studies have shown that cadralazine is superior to placebo, and has a similar blood pressure lowering effect to hydralazine, dihydralazine and prazosin in patients not controlled by beta-blocker and/or diuretic but who continued to receive these treatments. Similarly, cadralazine and chlorthalidone were equally effective in reducing blood pressure in resting hypertensive patients but cadralazine shows an advantage in reducing the pressor response in exercising patients. Cadralazine is well tolerated when administered with a beta-blocker or diuretic. Most adverse effects become less frequent and severe with continued use, occur more frequently at dosages of 20 mg/day or more, and do not generally require withdrawal of therapy. Manifestations of the drug's vasodilating properties such as headache, asthenia, dizziness, palpitations and flushing are the most commonly reported symptoms during cadralazine monotherapy, but these may be reduced during combination therapy. The drug does not appear to induce a systemic lupus-like erythematosus syndrome, as may occur with hydralazine, but additional clinical experience is required to completely exclude this possibility. The therapeutic potential of cadralazine cannot be clearly established until the present limited clinical base is expanded to include comparisons with other classes of vasodilating drugs (ACE inhibitors and calcium antagonists), and its utility in the management of other indications such as severe hypertension during pregnancy has been adequately explored.

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Patents

Patents

Sample Use Guides

In Vivo Use Guide
15 mg dose when the drug is administered as monotherapy. When administered in combination with other antihypertensive agents, a 10 mg daily dosage seems appropriate
Route of Administration: Oral
In Vitro Use Guide
The inhibitory effects of a hypotensive agent, cadralazine on the level of cytosolic Ca2+ ([Ca2+]cyt) and on contractions were examined in isolated vascular smooth muscle. Cadralazine slightly inhibited the transient norepinephrine-induced contraction in rabbit aorta and canine femoral, renal and mesenteric arteries and saphenous vein, and prostaglandin F2 alpha-induced contractions in canine basilar and coronary arteries.
Substance Class Chemical
Created
by admin
on Sat Dec 16 17:40:38 GMT 2023
Edited
by admin
on Sat Dec 16 17:40:38 GMT 2023
Record UNII
8T96I3U713
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CADRALAZINE
INN   JAN   MART.   MI   WHO-DD  
INN  
Official Name English
CADRALAZINE [JAN]
Common Name English
CADRALAZINE [MART.]
Common Name English
CADRAL
Brand Name English
CADRALAZINE [MI]
Common Name English
Cadralazine [WHO-DD]
Common Name English
ETHYL 6-(ETHYL(2-HYDROXYPROPYL)AMINO)-3-PYRIDAZINECARBAZATE
Common Name English
cadralazine [INN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C270
Created by admin on Sat Dec 16 17:40:38 GMT 2023 , Edited by admin on Sat Dec 16 17:40:38 GMT 2023
WHO-VATC QC02DB04
Created by admin on Sat Dec 16 17:40:38 GMT 2023 , Edited by admin on Sat Dec 16 17:40:38 GMT 2023
WHO-ATC C02DB04
Created by admin on Sat Dec 16 17:40:38 GMT 2023 , Edited by admin on Sat Dec 16 17:40:38 GMT 2023
Code System Code Type Description
NCI_THESAURUS
C81527
Created by admin on Sat Dec 16 17:40:38 GMT 2023 , Edited by admin on Sat Dec 16 17:40:38 GMT 2023
PRIMARY
MERCK INDEX
m1050
Created by admin on Sat Dec 16 17:40:38 GMT 2023 , Edited by admin on Sat Dec 16 17:40:38 GMT 2023
PRIMARY Merck Index
ChEMBL
CHEMBL2106561
Created by admin on Sat Dec 16 17:40:38 GMT 2023 , Edited by admin on Sat Dec 16 17:40:38 GMT 2023
PRIMARY
CAS
64241-34-5
Created by admin on Sat Dec 16 17:40:38 GMT 2023 , Edited by admin on Sat Dec 16 17:40:38 GMT 2023
PRIMARY
INN
4670
Created by admin on Sat Dec 16 17:40:38 GMT 2023 , Edited by admin on Sat Dec 16 17:40:38 GMT 2023
PRIMARY
EVMPD
SUB06042MIG
Created by admin on Sat Dec 16 17:40:38 GMT 2023 , Edited by admin on Sat Dec 16 17:40:38 GMT 2023
PRIMARY
DRUG BANK
DB13452
Created by admin on Sat Dec 16 17:40:38 GMT 2023 , Edited by admin on Sat Dec 16 17:40:38 GMT 2023
PRIMARY
FDA UNII
8T96I3U713
Created by admin on Sat Dec 16 17:40:38 GMT 2023 , Edited by admin on Sat Dec 16 17:40:38 GMT 2023
PRIMARY
MESH
C031877
Created by admin on Sat Dec 16 17:40:38 GMT 2023 , Edited by admin on Sat Dec 16 17:40:38 GMT 2023
PRIMARY
SMS_ID
100000081570
Created by admin on Sat Dec 16 17:40:38 GMT 2023 , Edited by admin on Sat Dec 16 17:40:38 GMT 2023
PRIMARY
EPA CompTox
DTXSID4048725
Created by admin on Sat Dec 16 17:40:38 GMT 2023 , Edited by admin on Sat Dec 16 17:40:38 GMT 2023
PRIMARY
PUBCHEM
2515
Created by admin on Sat Dec 16 17:40:38 GMT 2023 , Edited by admin on Sat Dec 16 17:40:38 GMT 2023
PRIMARY
DRUG CENTRAL
461
Created by admin on Sat Dec 16 17:40:38 GMT 2023 , Edited by admin on Sat Dec 16 17:40:38 GMT 2023
PRIMARY
Related Record Type Details
ENANTIOMER -> RACEMATE
ENANTIOMER -> RACEMATE
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ACTIVE MOIETY