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Butaperazine

HCID 12598
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Basic information

CAS
653-03-2
Standard SMILES
CCCC(=O)c1ccc2c(c1)N(CCCN1CCN(C)CC1)c1ccccc1S2
InChIKey
DVLBYTMYSMAKHP-UHFFFAOYSA-N
Molecular formula
C24H31N3OS
Average molar mass
409.6 g/mol
Monoisotopic mass
409.21878379

Overview

Butaperazine is a member of phenothiazines.

Names & identifiers

Preferred name
Butaperazine
IUPAC
1-[10-[3-(4-methylpiperazin-1-yl)propyl]phenothiazin-2-yl]butan-1-one
English name
butaperazine
Molecular formula
C24H31N3OS
Molecular weight
409.59

Names & synonyms

BUTAPERAZINEButyrylperazine653-03-2MegalectilRandolectilEmerexRepoiseRiker 595Bayer 1362ButyrylyperazinePerazine, butyryl-Perazine, (1-oxobutyl)-
Show more names
Butaperazina1-[10-[3-(4-methylpiperazin-1-yl)propyl]phenothiazin-2-yl]butan-1-one1-[10-[3-(4-Methyl-1-piperazinyl)propyl]-10H-phenothiazin-2-yl]-1-butanone1-Butanone, 1-[10-[3-(4-methyl-1-piperazinyl)propyl]-10H-phenothiazin-2-yl]-
AHR-712AHR 712AHR-3000RIKER-595BAYER-13621-Butanone, 1-(10-(3-(4-methyl-1-piperazinyl)propyl)-10H-phenothiazin-2-yl)-TXP4T9106S1-(10-(3-(4-Methyl-1-piperazinyl)propyl)phenothiazin-2-yl)-1-butanone

Database identifiers

CAS
653-03-2
PubChem CID
12598
DTXSID
DTXSID1022712
ChEMBL
CHEMBL1697826
ChEBI
CHEBI:135663
UNII
TXP4T9106S
EC Number
211-493-9
Nikkaji
J7.078E

Properties

Computed structural properties

XLogP
5
Topological polar surface area
52.1 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
5
Rotatable bonds
7
Heavy atoms
29
Formal charge
0
Complexity
536

Experimental & physicochemical properties

LogP4.83
Solubility · 2 items

1 G IN 400 ML WATER; SOL IN DIMETHYLFORMAMIDE; SPARINGLY SOL IN ALCOHOL & METHANOL; INSOL IN ACETONE, CHLOROFORM, & ETHER /MALEATE/

SOL OF THE FREE BASE IN ARTIFICIAL INTESTINAL JUICE WAS 283 MG/100 ML AT PH 6, DECR TO 4.9 MG/100 ML AT PH 8

Human DrugsPharmaceuticals
Boiling Point270-280 °C @ 0.05 mm Hg
Melting PointMP: 180-182 °C /Maleate/
Stability/Shelf LifeUNSTABLE IN LIGHT (SUBJECT TO OXIDATIVE DEGRADATION) & EXCESSIVE HEAT /MALEATE/
Other Experimental Properties · 3 items

PRACTICALLY ODORLESS & HAS MODERATELY BITTER TASTE, NOT APPRECIABLY HYGROSCOPIC /MALEATE/

BRIGHT-YELLOW POWDER /MALEATE/

Crystals from carbon tetrachloride /Maleate/

Physicochemical properties

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

Hazard information

FDA Requirements · 1 item

Manufacturers, packers, and distributors of drug and drug products for human use are responsible for complying with the labeling, certification, and usage requirements as prescribed by the Federal Food, Drug, and Cosmetic Act, as amended (secs 201-902, 52 Stat. 1040 et seq., as amended; 21 U.S.C. 321-392).

Safety & protection

Disposal Methods · 1 item

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Toxicology

Interactions · 5 items

THE PHENOTHIAZINES WITH LOW POTENCY...MARKEDLY AFFECT THE ACTIONS OF A NUMBER OF OTHER DRUGS, & COGNIZANCE MUST BE TAKEN OF THIS FACT. ... PATIENTS SHOULD ALSO BE WARNED TO EXPECT ENHANCEMENT OF THE EFFECTS OF ALCOHOL. ...THE PHENOTHIAZINES CAN PROMOTE HYPOTENSION, POSSIBLY DUE TO THEIR ALPHA-ADRENERGIC BLOCKING PROPERTIES. THUS, THE INTERACTION BETWEEN PHENOTHIAZINE AND ANTIHYPERTENSIVES CAN BE QUITE UNPREDICTABLE.

...CONTRAINDICATED IN COMATOSE PT WHO HAVE RECEIVED LARGE AMT OF CENTRAL NERVOUS SYSTEM DEPRESSANT DRUGS (...BARBITURATES, NARCOTICS, ETC)... /PHENOTHIAZINES/

ROUTINE ADMIN OF ANTIPARKINSONISM AGENTS SHOULD BE AVOIDED WITH MOST ANTIPSYCHOTIC DRUG REGIMENS. /PHENOTHIAZINES/

...PHENOTHIAZINES...MAY PRODUCE ADDITIVE HYPOTENSIVE EFFECTS WITH PROPRANOLOL. /PHENOTHIAZINES/

For more Interactions (Complete) data for BUTAPERAZINE (37 total), please visit the HSDB record page.

Milk ConcentrationsPHENOTHIAZINES ... MAY APPEAR IN MILK OF NURSING MOTHERS... /PHENOTHIAZINES, HUMAN, ORAL, IM/

Chemistry & industry

Pharmacology

ATC Code · 2 items

N - Nervous system

QN - Nervous system

Mechanism of Action · 2 items

THERE IS AN ADENYLATE CYCLASE IN LIMBIC SYSTEM, AS WELL AS IN CAUDATE NUCLEUS, THAT IS SPECIFICALLY ACTIVATED BY DOPAMINE. ...ACTIVATION OF...ENZYME IS... BLOCKED BY...PHENOTHIAZINES. ...THERAPEUTIC EFFICACY & SIDE EFFECTS MAY RELATE TO INHIBITION OF DOPAMINE ACTIVATION OF ADENYLATE CYCLASE. /PHENOTHIAZINES/

...PHENOTHIAZINES, BLOCK DOPAMINE RECEPTORS & INCR TURNOVER RATE OF DOPAMINE IN CORPUS STRIATUM. INCR TURNOVER RATE IS BELIEVED TO BE RESULT OF NEURONAL FEEDBACK MECHANISM. ...FIRING OF.../IDENTIFIED DOPAMINERGIC NEURONS IN SUBSTANTIA NIGRA & VENTRAL TEGMENTAL AREAS/ IS INCR BY ANTIPSYCHOTIC PHENOTHIAZINES. /PHENOTHIAZINES/

Biological Half-LifeBUTAPERAZINE (10-60 MG ORALLY) HAD AVG PEAK SERUM LEVELS OF 215 NG/ML IN HUMANS AND AN INITIAL RAPID PHASE HALF-LIFE OF 4 HR AND A SLOWER PHASE HALF-LIFE OF 12 HR. SERUM BUTAPERAZINE LEVELS WERE PROPORTIONAL TO THE DOSE ADMINISTERED.
Metabolism/Metabolites · 2 items

AFTER CHRONIC ADMIN OF PIPERAZINE-SUBSTITUTED PHENOTHIAZINE DRUGS...TO RATS, TISSUES CONTAINED DRUG METABOLITES, IN WHICH PIPERAZINE RING FISSION BY MULTIPLE OXIDATIVE N-DEALKYLATION HAD OCCURRED TO GIVE SUBSTITUTED ETHYLENEDIAMINE. /PIPERAZINE PHENOTHIAZINES/

IN RATS & DOGS, PRINCIPAL FECAL METABOLITES OF BUTAPERAZINE DIMALEATE RESULT FROM HYDROXYLATION OF PHENOTHIAZINE RING-SYSTEM & OXIDATIVE N-DEMETHYLATION. BUTAPERAZINE SULFOXIDE, BUTAPERAZINE SULFONE, & REDN PRODUCT OF BUTYRYL SIDE-CHAIN CARBONYL GROUP MAKE UP MINOR METABOLITES. /DIMALEATE/

Absorption, Distribution and Excretion · 3 items

NEUROLEPTIC CONCN-THERAPEUTIC RESPONSE CURVES EXAMINED FOR BUTAPERAZINE IN 10 SCHIZOPHRENIC PT DURING FIRST 12 DAYS OF TREATMENT. RESULTS SHOWED BUTAPERAZINE BOUND TO RED BLOOD CELLS WAS MORE STRONGLY CORRELATED WITH THERAPEUTIC RESPONSE THAN WAS PLASMA CONCN.

IN A STUDY ON 2 GROUPS OF NONRESPONDING SCHIZOPHRENICS AND ONE GROUP OF CLINICALLY RESPONDING PT WITH AFFECTIVE DISORDERS, THE NONRESPONDERS HAD 2 TO 7 TIMES LOWER LEVELS OF BUTAPERAZINE, 40 MG TWICE DAILY, IN PLASMA AND RED BLOOD CELLS AFTER A SINGLE DOSE OR CHRONIC DOSING.

Related reactions

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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
More actions
New noteNew reactionRequest quotes
Boiling point
0.05 · bp0.05 270-280°
Density
1.138 · 1.138±0.06 g/cm3(Predicted)
pka
7.66 · 7.66±0.10(Predicted)
FDA UNII
4 T9106S · TXP4T9106S
ATC code
5 AB09 · N05AB09
Hazardous Substances Data
653 · 653-03-2(Hazardous Substances Data)
Non-Human Toxicity ExcerptsBUTAPERAZINE (1 MG/KG SC) DIMINISHED EXPLORATORY BEHAVIOR IN MICE.
Antidote and Emergency Treatment · 1 item

EXTRAPYRAMIDAL SYMPTOMS...RELIEVED WITH BARBITURATES, METHYLPHENIDATE HYDROCHLORIDE...ANTI-PARKINSON DRUGS...BENZTROPINE MESYLATE...TRIHEXYPHENIDYL HYDROCHLORIDE...DIPHENHYDRAMINE HYDROCHLORIDE...IN SEVERE CASES, SUPPORTIVE THERAPY...MAINTAINING CLEAR AIRWAY & ADEQUATE HYDRATION. /HYDROCHLORIDE/

Regulatory information

FDA Requirements · 1 item

Manufacturers, packers, and distributors of drug and drug products for human use are responsible for complying with the labeling, certification, and usage requirements as prescribed by the Federal Food, Drug, and Cosmetic Act, as amended (secs 201-902, 52 Stat. 1040 et seq., as amended; 21 U.S.C. 321-392).

Safety data

Hazardous Substances Data
653-03-2(Hazardous Substances Data)

EIGHT OF 10 CHRONIC SCHIZOPHRENIC PT RECEIVED A 40 MG LOADING DOSE OF BUTAPERAZINE AND THEN WERE TITRATED UNTIL A THERAPEUTIC RESPONSE WAS OBTAINED. THRICE DAILY USE OF THE DRUG SHOWED A HIGHER WHOLE BLOOD STEADY STATE DRUG PLASMA LEVEL THAN THE ONCE A DAY USE OF THE SAME TOTAL DAILY DOSE.

Uses & manufacturing

UsesAntipsychotic
Methods of Manufacturing · 2 items

Hoerlein et al, German patent 1,120,451 (1961 to Bayer), CA 57, 4677c (1962).

1-METHYLPIPERAZINE IS CONDENSED WITH 10-(3-CHLOROPROPYL)PHENOTHIAZIN-2-YL PROPYL KETONE BY REFLUXING MIXT IN INERT SOLVENT IN PRESENCE OF DEHYDROCHLORINATING AGENT SUCH AS SODAMIDE. RESULTING BUTAPERAZINE IS THEN REACTED WITH DOUBLE EQUIMOLAR PORTION OF MALEIC ACID. ... US PATENT 2,985,654. /MALEATE/

Formulations/PreparationsTABLETS: 5, 10, & 25 MG (OF BASE AS MALEATE). /MALEATE/
Use ClassificationPharmaceuticals
General Manufacturing InformationA FEW AVAIL AGENTS...ARE NOW KNOWN TO HAVE INFERIOR ANTIPSYCHOTIC EFFECTS OR...ARE NO LONGER COMMONLY USED IN PSYCHIATRIC PT. THESE INCL BUTAPERAZINE...

Applications

UsesAntipsychotic.

Upstream & downstream products

Upstream raw materials

Sodium amideSodium hydroxide

Downstream products

bis[1-[3-[2-(1-oxobutyl)-10H-phenothiazin-2-yl]propyl]-4-methylpiperazin-1-yl] maleate

Additional notes

DefinitionChEBI: Butaperazine is a member of phenothiazines.