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Home > Encyclopedia > Diphenidol

Diphenidol

pharmaceutical raw materials
Diphenidol structure

Diphenidol 

structure
  • CAS No:

    972-02-1

  • Formula:

    C21H27NO

  • Chemical Name:

    Diphenidol

  • Synonyms:

    1-Piperidinebutanol,α,α-diphenyl-;α,α-Diphenyl-1-piperidinebutanol;SKF 478;Difenidol;Diphenidol;Nometic;Benzhydrol,α-(3-piperidinopropyl)-;Diphenadol;1,1-Diphenyl-4-piperidino-1-butanol;Diphenyl[3-(1-piperidyl)propyl]carbinol;Cephadol;Avomol;Lansenol

  • Categories:

    Active Pharmaceutical Ingredients  >  Digestive System Drugs

Description

ChEBI: A tertiary alcohol that is butan-1-ol substituted by two phenyl groups at position 1 and a piperidin-1-yl group at position 4.


Solid


Diphenidol is a tertiary alcohol that is butan-1-ol substituted by two phenyl groups at position 1 and a piperidin-1-yl group at position 4. It has a role as an antiemetic. It is a member of piperidines, a tertiary alcohol and a member of benzenes.|Diphenidol is an antiemetic agent used in the treatment of vomiting and vertigo. Diphenidol overdose may result in serious toxicity in children.|Diphenidol is an Antiemetic. The physiologic effect of diphenidol is by means of Emesis Suppression.

Diphenidol Basic Attributes

309.45

309.45

213-540-9

NQO8R319LY

DTXSID3022950

NEEDLES FROM PETROLEUM ETHER|WHITE CRYSTALLINE POWDER

2933399090

Characteristics

23.5

4.3

Solid

1.066 g/cm3

104-105 °C

153-157 °C @ Press: 0.2 Torr

233.5ºC

1.5614 (estimate)

5.87e-03 g/L

LD50 s.c. in rats: 50 mg/kg (Goldenthal)

ODORLESS

SLIGHTLY BITTER TASTE

Safety Information

STABLE IN LIGHT & AIR

Toxicity

Symptoms of overdose include drowsiness (severe); shortness of breath or troubled breathing; unusual tiredness or weakness (severe).

LD50 MICE ORAL 430 MG/KG /HCL/|LD50 MICE INTRAPERITONEAL 105 MG/KG /HCL/|LD50 MICE INTRAVENOUS 37 MG/KG /HCL/|LD50 RATS ORAL 515 MG/KG /HCL/|For more Non-Human Toxicity Values (Complete) data for DIPHENIDOL (6 total), please visit the HSDB record page.

Drug Information

For use in the prevention and symptomatic treatment of peripheral (labyrinthine) vertigo and associated nausea and vomiting that occur in such conditions as Meniere's disease and surgery of the middle and inner ear. Also for the control of nausea and vomiting associated with postoperative states, malignant neoplasms, labyrinthine disturbances, antineoplastic agent therapy, radiation sickness, and infectious diseases.|FDA Label

Antiemetics; Histamine H1 Antagonists|...ANTIEMETIC AGENT FOR ORAL, RECTAL, IM, OR IV ADMIN, USEFUL IN MGMNT OF NAUSEA & VOMITING ASSOC WITH INFECTIOUS DISEASES, MALIGNANCIES, RADIATION SICKNESS, GENERAL ANESTHESIA, TREATMENT WITH ANTINEOPLASTIC AGENTS. ...ALSO USEFUL IN TREATMENT OF VERTIGO OF VESTIBULAR ORIGIN.|IN ADULTS, THIS DRUG ALSO IS EFFECTIVE IN...LABYRINTHITIS FOLLOWING SURGERY OF MIDDLE & INNER EAR, & MENIERE'S DISEASE. ITS USE IN TREATMENT OF VERTIGO IN CHILDREN HAS NOT BEEN INVESTIGATED. /HCL/

SINCE DIPHENIDOL DOES POSSESS PARASYMPATHOLYTIC PROPERITES, IT SHOULD BE USED CAUTIOUSLY IN PT WITH GLAUCOMA, PROSTATIC HYPERTROPHY, PEPTIC ULCER, PYLORIC OR DUODENAL OBSTRUCTION, OR CARDIOSPASM.|...IT IS NOT RECOMMENDED FOR USE IN NAUSEA & VOMITING OF PREGNANCY, SINCE ITS SAFE USE IN THIS CONDITION HAS NOT BEEN ESTABLISHED.

Diphenidol is used for control of nausea and vomiting. It has an antivertigo effect on the vestibular apparatus, inhibiting the chemoreceptor trigger zone to control nausea and vomiting, thus preventing motion sickness.

Drugs used to prevent NAUSEA or VOMITING. (See all compounds classified as Antiemetics.)

Well absorbed from gastrointestinal tract following oral administration.

IN DOGS & IN MAN, PRINCIPAL URINARY METABOLITE OF DIPHENIDOL...WAS N-(4,4-DIPHENYL-4-HYDROXYBUTYL)-DELTA-AMINOVALERIC ACID...(NOT LESS THAN 50% OF DOSE)... MINOR URINARY METABOLITES INCL A PHENOL...& A LACTAM...

4 hours

The mechanism by which diphenidol exerts its antiemetic and antivertigo effects is not precisely known. It is thought to diminish vestibular stimulation and depress labyrinthine function and as an antimuscarinic agent. An action on the medullary chemoreceptive trigger zone may also be involved in the antiemetic effect. Diphenidol has no significant sedative, tranquilizing, or antihistaminic action. It has a weak peripheral anticholinergic effect.|EXPTL, IT HAS BEEN SHOWN TO EXHIBIT WEAK PARASYMPATHOLYTIC ACTIONS, BUT TO LACK SIGNIFICANT SEDATIVE, TRANQUILIZING, OR ANTIHISTAMINIC PROPERTIES.|.../DIPHENIDOL/ IS THOUGHT TO ACT UPON AURAL VESTIBULAR APPARATUS...

...AUDITORY & VISUAL HALLUCINATIONS, DISORIENTATION, & CONFUSION HAVE BEEN REPORTED. OTHER UNTOWARD EFFECTS SUCH AS DROWSINESS, DRY MOUTH, DIZZINESS, SKIN RASH, HEARTBURN, HEADACHE, NAUSEA...MALAISE, ETC HAVE BEEN INFREQUENT & MINOR IN NATURE.

Cefadol

Diphenidol Use and Manufacturing

Methods of Manufacturing

MIESCHER, MARXER, US PATENT 2,411,644 (1946 TO CIBA); BARRETT, WILKINSON, BRITISH PATENT 683,950 (1952 TO WELLCOME FOUNDATION), CA 48, 2112E (1954).

Uses

Anti-emetic.

HCL...CEFADOL. ... VONTROL IS ALSO AVAILABLE AS THE...PAMOATE.|SUPPOSITORIES: 25 TO 50 MG; ORAL SUSPENSION (AS THE PAMOATE): 20 MG/5 ML

DIPHENIDOL IS DISSOLVED IN SUITABLE SOLVENT & REACTED WITH HYDROGEN CHLORIDE. /HCL/

Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients

Computed Properties

Molecular Weight:309.4
XLogP3:4.2
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:6
Exact Mass:309.209264485
Monoisotopic Mass:309.209264485
Topological Polar Surface Area:23.5
Heavy Atom Count:23
Complexity:307
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Drug Function and Efficacy

No specific role mentioned

This ingredient has been used in drugs with the following functions (note: it does not mean that the ingredient itself has the following health functions)

Related Drugs

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