915-30-0 Usage
Uses
Used in Pharmaceutical Industry:
Diphenoxylate is used as an anti-diarrheal agent for treating diarrhea. It works by slowing down the movement of the gut, allowing more time for water to be absorbed and resulting in firmer stools.
Indications
Diphenoxylate (marketed in combination with atropine
as Lomotil in the United States) is chemically related
to both analgesic and anticholinergic compounds.
It is as effective in the treatment of diarrhea as the
opium derivatives, and at the doses usually employed, it
has a low incidence of central opioid actions. Diphenoxylate
is rapidly metabolized by ester hydrolysis to the
biologically active metabolite difenoxylic acid.
World Health Organization (WHO)
Diphenoxylate, a derivative of pethidine without analgesic
activity, is used in the symptomatic treatment of acute and chronic diarrhoea to
reduce intestinal motility. There is no clear evidence that it has any beneficial effect
in diminishing fluid losses and it has been associated with central nervous system
toxicity, particularly in children, which results in anorexia, nausea and vomiting,
headache, drowsiness, confusion, insomnia, dizziness, restlessness, euphoria and
depression. The World Health Organization recommends that diphenoxylate should
not be used for the management of diarrhoea in children and many countries have
since withdrawn products containing Diphenoxylate indicated for paediatric use.
(Reference: (WHORUD) The Rational Use of Drugs, , , 1990)
Clinical Use
Lomotil is recommended as adjunctive therapy in the management
of diarrhea. It is contraindicated in children under
2 years old and in patients with obstructive jaundice.
Side effects
Adverse reactions often caused by the atropine in the
preparation include anorexia, nausea, pruritus, dizziness,
and numbness of the extremities.
Synthesis
Diphenoxylate, ethyl ester of 1-(3-cyano-3,3-diphenylpropyl)-
4-phenylpiperidine-4-carboxylic acid (3.1.58), is also a drug of 4-phenylpiperidine series. In
practice there are two ways of making it. The first way is by the alkylation of the ethyl ester
of 4-phenylpiperidine-4-carboxylic acid (3.1.56) with 2,2-diphenyl-4-bromobutyronitrile,
which in turn is synthesized from 1-benzyl-4-phenyl-4-cyanopiperidine. The product undergoes ethanolysis in the presence of acid, followed by benzylation. The second way is a synthesis accomplished by alkylation of diphenylacetonitrile using ethyl ester of
1-(2-chloroethyl)-4-phenylpiperidine-4-carboxylic acid (3.1.57), which is synthesized by reaction of ethyl ester of 4-phenylpiperidine-4-carboxylic acid with β-chloroethanol or ethylenoxide with the subsequent substitution of hydroxyl group, which results from the opening of the epoxide ring, by chlorine via action of thionyl chloride [37,38].
Check Digit Verification of cas no
The CAS Registry Mumber 915-30-0 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 9,1 and 5 respectively; the second part has 2 digits, 3 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 915-30:
(5*9)+(4*1)+(3*5)+(2*3)+(1*0)=70
70 % 10 = 0
So 915-30-0 is a valid CAS Registry Number.
InChI:InChI=1/C30H32N2O2/c1-2-34-28(33)29(25-12-6-3-7-13-25)18-21-32(22-19-29)23-20-30(24-31,26-14-8-4-9-15-26)27-16-10-5-11-17-27/h3-17H,2,18-23H2,1H3
915-30-0Relevant academic research and scientific papers
Combination of selected opioids with muscarine antagonists for treating urinary incontinence
-
, (2008/06/13)
Active compound combinations of compounds of group A, particularly opioids, and compounds of group B, particularly anti-muscarine agents and other substances suitable for treatment of an increased urge to urinate or urinary incontinence. Related pharmaceutical formulations and methods of treatment of an increased urge to urinate or urinary incontinence are also provided.
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