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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
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
130 ng/g
CLINICAL TRIAL
10.1007/BF03189745
5 mg single, oral
dose: 5 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CADRALAZINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
210 ng/g
CLINICAL TRIAL
10.1007/BF03189745
10 mg single, oral
dose: 10 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CADRALAZINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
379 ng/g
CLINICAL TRIAL
10.1007/BF03189745
20 mg single, oral
dose: 20 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CADRALAZINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
224 μg/L
15 mg single, oral
dose: 15 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CADRALAZINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
568 μg/L
30 mg single, oral
dose: 30 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CADRALAZINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
749 pmol/mL
10 mg single, oral
dose: 10 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CADRALAZINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
611 pmol/mL
10 mg single, oral
dose: 10 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CADRALAZINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
330 ng × h/g
CLINICAL TRIAL
10.1007/BF03189745
5 mg single, oral
dose: 5 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CADRALAZINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
621 ng × h/g
CLINICAL TRIAL
10.1007/BF03189745
10 mg single, oral
dose: 10 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CADRALAZINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
1168 ng × h/g
CLINICAL TRIAL
10.1007/BF03189745
20 mg single, oral
dose: 20 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CADRALAZINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
632 μg × h/L
15 mg single, oral
dose: 15 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CADRALAZINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
2888 μg × h/L
30 mg single, oral
dose: 30 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CADRALAZINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
1884 pmol × h/mL
10 mg single, oral
dose: 10 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CADRALAZINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
1884 pmol × h/mL
10 mg single, oral
dose: 10 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CADRALAZINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
2.4 h
CLINICAL TRIAL
10.1007/BF03189745
5 mg single, oral
dose: 5 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CADRALAZINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
2.4 h
CLINICAL TRIAL
10.1007/BF03189745
10 mg single, oral
dose: 10 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CADRALAZINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
2.3 h
CLINICAL TRIAL
10.1007/BF03189745
20 mg single, oral
dose: 20 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CADRALAZINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
1.7 h
15 mg single, oral
dose: 15 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CADRALAZINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
3.1 h
30 mg single, oral
dose: 30 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CADRALAZINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
2.38 h
10 mg single, oral
dose: 10 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CADRALAZINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
Doses

Doses

DosePopulationAdverse events​
30 mg single, oral
Highest studied dose
Dose: 30 mg
Route: oral
Route: single
Dose: 30 mg
Sources:
unhealthy
Health Status: unhealthy
Sex: M+F
Food Status: UNKNOWN
Sources:
Other AEs: Headache, Tachycardia...
Other AEs:
Headache (5 patients)
Tachycardia (6 patients)
Postural hypotension (5 patients)
Dizziness (2 patients)
Asthenia (2 patients)
Lacrimation (2 patients)
Sources:
AEs

AEs

AESignificanceDosePopulation
Asthenia 2 patients
30 mg single, oral
Highest studied dose
Dose: 30 mg
Route: oral
Route: single
Dose: 30 mg
Sources:
unhealthy
Health Status: unhealthy
Sex: M+F
Food Status: UNKNOWN
Sources:
Dizziness 2 patients
30 mg single, oral
Highest studied dose
Dose: 30 mg
Route: oral
Route: single
Dose: 30 mg
Sources:
unhealthy
Health Status: unhealthy
Sex: M+F
Food Status: UNKNOWN
Sources:
Lacrimation 2 patients
30 mg single, oral
Highest studied dose
Dose: 30 mg
Route: oral
Route: single
Dose: 30 mg
Sources:
unhealthy
Health Status: unhealthy
Sex: M+F
Food Status: UNKNOWN
Sources:
Headache 5 patients
30 mg single, oral
Highest studied dose
Dose: 30 mg
Route: oral
Route: single
Dose: 30 mg
Sources:
unhealthy
Health Status: unhealthy
Sex: M+F
Food Status: UNKNOWN
Sources:
Postural hypotension 5 patients
30 mg single, oral
Highest studied dose
Dose: 30 mg
Route: oral
Route: single
Dose: 30 mg
Sources:
unhealthy
Health Status: unhealthy
Sex: M+F
Food Status: UNKNOWN
Sources:
Tachycardia 6 patients
30 mg single, oral
Highest studied dose
Dose: 30 mg
Route: oral
Route: single
Dose: 30 mg
Sources:
unhealthy
Health Status: unhealthy
Sex: M+F
Food Status: UNKNOWN
Sources:
PubMed

PubMed

TitleDatePubMed
[Effects of cadralazine on the respiration, circulation, kidney, autonomic nervous system, digestive system, blood and so on].
1988-04
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 Wed Apr 02 09:26:11 GMT 2025
Edited
by admin
on Wed Apr 02 09:26:11 GMT 2025
Record UNII
8T96I3U713
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CADRAL
Preferred Name English
CADRALAZINE
INN   JAN   MART.   MI   WHO-DD  
INN  
Official Name English
CADRALAZINE [JAN]
Common Name English
CADRALAZINE [MART.]
Common 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 Wed Apr 02 09:26:11 GMT 2025 , Edited by admin on Wed Apr 02 09:26:11 GMT 2025
WHO-VATC QC02DB04
Created by admin on Wed Apr 02 09:26:11 GMT 2025 , Edited by admin on Wed Apr 02 09:26:11 GMT 2025
WHO-ATC C02DB04
Created by admin on Wed Apr 02 09:26:11 GMT 2025 , Edited by admin on Wed Apr 02 09:26:11 GMT 2025
Code System Code Type Description
NCI_THESAURUS
C81527
Created by admin on Wed Apr 02 09:26:11 GMT 2025 , Edited by admin on Wed Apr 02 09:26:11 GMT 2025
PRIMARY
MERCK INDEX
m1050
Created by admin on Wed Apr 02 09:26:11 GMT 2025 , Edited by admin on Wed Apr 02 09:26:11 GMT 2025
PRIMARY Merck Index
ChEMBL
CHEMBL2106561
Created by admin on Wed Apr 02 09:26:11 GMT 2025 , Edited by admin on Wed Apr 02 09:26:11 GMT 2025
PRIMARY
CAS
64241-34-5
Created by admin on Wed Apr 02 09:26:11 GMT 2025 , Edited by admin on Wed Apr 02 09:26:11 GMT 2025
PRIMARY
INN
4670
Created by admin on Wed Apr 02 09:26:11 GMT 2025 , Edited by admin on Wed Apr 02 09:26:11 GMT 2025
PRIMARY
EVMPD
SUB06042MIG
Created by admin on Wed Apr 02 09:26:11 GMT 2025 , Edited by admin on Wed Apr 02 09:26:11 GMT 2025
PRIMARY
DRUG BANK
DB13452
Created by admin on Wed Apr 02 09:26:11 GMT 2025 , Edited by admin on Wed Apr 02 09:26:11 GMT 2025
PRIMARY
FDA UNII
8T96I3U713
Created by admin on Wed Apr 02 09:26:11 GMT 2025 , Edited by admin on Wed Apr 02 09:26:11 GMT 2025
PRIMARY
MESH
C031877
Created by admin on Wed Apr 02 09:26:11 GMT 2025 , Edited by admin on Wed Apr 02 09:26:11 GMT 2025
PRIMARY
SMS_ID
100000081570
Created by admin on Wed Apr 02 09:26:11 GMT 2025 , Edited by admin on Wed Apr 02 09:26:11 GMT 2025
PRIMARY
EPA CompTox
DTXSID4048725
Created by admin on Wed Apr 02 09:26:11 GMT 2025 , Edited by admin on Wed Apr 02 09:26:11 GMT 2025
PRIMARY
PUBCHEM
2515
Created by admin on Wed Apr 02 09:26:11 GMT 2025 , Edited by admin on Wed Apr 02 09:26:11 GMT 2025
PRIMARY
DRUG CENTRAL
461
Created by admin on Wed Apr 02 09:26:11 GMT 2025 , Edited by admin on Wed Apr 02 09:26:11 GMT 2025
PRIMARY
Related Record Type Details
ENANTIOMER -> RACEMATE
ENANTIOMER -> RACEMATE
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ACTIVE MOIETY