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Chemistry

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Also known as: 8001-79-4, Ricinus oil, Venelex, Xenaderm, Vegetable oil, Cosmetol
Molecular Formula
C57H104O9
Molecular Weight
933.4  g/mol
InChI Key
ZEMPKEQAKRGZGQ-AAKVHIHISA-N

Venelex
Oil obtained from seeds of Ricinus communis that is used as a cathartic and as a plasticizer.
1 2D Structure

Venelex

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
2,3-bis[[(Z)-12-hydroxyoctadec-9-enoyl]oxy]propyl (Z)-12-hydroxyoctadec-9-enoate
2.1.2 InChI
InChI=1S/C57H104O9/c1-4-7-10-31-40-51(58)43-34-25-19-13-16-22-28-37-46-55(61)64-49-54(66-57(63)48-39-30-24-18-15-21-27-36-45-53(60)42-33-12-9-6-3)50-65-56(62)47-38-29-23-17-14-20-26-35-44-52(59)41-32-11-8-5-2/h25-27,34-36,51-54,58-60H,4-24,28-33,37-50H2,1-3H3/b34-25-,35-26-,36-27-
2.1.3 InChI Key
ZEMPKEQAKRGZGQ-AAKVHIHISA-N
2.1.4 Canonical SMILES
CCCCCCC(CC=CCCCCCCCC(=O)OCC(COC(=O)CCCCCCCC=CCC(CCCCCC)O)OC(=O)CCCCCCCC=CCC(CCCCCC)O)O
2.1.5 Isomeric SMILES
CCCCCCC(O)C/C=C\CCCCCCCC(=O)OCC(OC(=O)CCCCCCC/C=C\CC(O)CCCCCC)COC(=O)CCCCCCC/C=C\CC(O)CCCCCC
2.2 Synonyms
2.2.1 MeSH Synonyms

1. Oil, Castor

2.2.2 Depositor-Supplied Synonyms

1. 8001-79-4

2. Ricinus Oil

3. Venelex

4. Xenaderm

5. Vegetable Oil

6. Cosmetol

7. Neoloid

8. Phorbyol

9. Ricinol

10. Ricini Oleum

11. Ricirus Oil

12. Tangantangan Oil

13. Gold Bond

14. Oleum Ricini

15. Olio Di Ricino

16. Viscotrol C

17. Crystal O

18. Palma Christi Oil

19. Aromatic Castor Oil

20. Castor Oil Aromatic

21. Db Oil

22. Ricinus Communis Oil

23. Castor Oil [jan]

24. Lavco

25. Castor Oil, Aromatic

26. Oil Of Palma Christi

27. Caswell No. 165b

28. Olio Di Ricino [italian]

29. Castor Oil, Aromatic [jan]

30. Optase

31. Unii-d5340y2i9g

32. Fema No. 2263

33. Ccris 4596

34. Hsdb 1933

35. Castor Oil (ricinus Communis L.)

36. Nci-c55163

37. Einecs 232-293-8

38. Epa Pesticide Chemical Code 031608

39. Castor Oil [usp:jan]

40. Castor Oil [oil, Edible]

41. Schembl12939325

42. 2,3-bis[[(z)-12-hydroxyoctadec-9-enoyl]oxy]propyl (z)-12-hydroxyoctadec-9-enoate

43. D5340y2i9g

44. Akos037515507

45. 1-o,2-o,3-o-tris[(z)-12-hydroxy-9-octadecenoyl]glycerol

2.3 Create Date
2007-02-09
3 Chemical and Physical Properties
Molecular Weight 933.4 g/mol
Molecular Formula C57H104O9
XLogP317.8
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count9
Rotatable Bond Count53
Exact Mass932.76803489 g/mol
Monoisotopic Mass932.76803489 g/mol
Topological Polar Surface Area140 Ų
Heavy Atom Count66
Formal Charge0
Complexity1110
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count3
Defined Bond Stereocenter Count3
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Therapeutic Uses

Cathartics; Emollients; Pharmaceutic Aids

National Library of Medicine's Medical Subject Headings online file (MeSH, 1999)


Therapeutically, castor oil has been administered orally for its laxative action... /Former use/

Rowe, R.C., Sheskey, P.J., Quinn, M.E.; (Eds.), Handbook of Pharmaceutical Excipients 6th edition Pharmaceutical Press, London, England 2009, p. 126


Castor oil is used in cosmetics and foods and orally, parenterally, and topically in pharmaceutical formulations. It is generally regarded as a relatively nontoxic and nonirritant material when used as an excipient.

Rowe, R.C., Sheskey, P.J., Quinn, M.E.; (Eds.), Handbook of Pharmaceutical Excipients 6th edition Pharmaceutical Press, London, England 2009, p. 127


...It is usually administered only when prompt, thorough evacuation of the bowel is desired, as in preparation for certain radiological examinations. /Former/

Hardman, J.G., L.E. Limbird, P.B. Molinoff, R.W. Ruddon, A.G. Goodman (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 9th ed. New York, NY: McGraw-Hill, 1996., p. 925


For more Therapeutic Uses (Complete) data for Castor oil (13 total), please visit the HSDB record page.


4.2 Drug Warning

Castor oil has been used therapeutically as a laxative and oral administration of large quantities may cause nausea, vomiting, colic, and severe purgation. It should not be given when intestinal obstruction is present.

Rowe, R.C., Sheskey, P.J., Quinn, M.E.; (Eds.), Handbook of Pharmaceutical Excipients 6th edition Pharmaceutical Press, London, England 2009, p. 127


Castor oil is contraindicated in pregnant or menstruating women.

American Hospital Formulary Service. Volumes I and II. Washington, DC: American Society of Hospital Pharmacists, to 1984., p. 56:12


... Should not be taken late in the day with the expectation of sleeping.

Hardman, J.G., L.E. Limbird, P.B. Molinoff, R.W. Ruddon, A.G. Goodman (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 9th ed. New York, NY: McGraw-Hill, 1996., p. 924


Sensitivity to castor oil when used medicinally is extremely rare.

International Labour Office. Encyclopedia of Occupational Health and Safety. Volumes I and II. New York: McGraw-Hill Book Co., 1971., p. 269


For more Drug Warnings (Complete) data for Castor oil (12 total), please visit the HSDB record page.


4.3 Minimum/Potential Fatal Human Dose

2(?). 2= slightly toxic: probable oral lethal dose (human): 5-15 g/kg, between 1 pint and 1 quart for 70 kg person (150 lb).

Gosselin, R.E., H.C. Hodge, R.P. Smith, and M.N. Gleason. Clinical Toxicology of Commercial Products. 4th ed. Baltimore: Williams and Wilkins, 1976., p. II-152


4.4 Drug Indication

Indicated for over-the-counter use as a laxative for oral use and as a soothing agent for topical use on skin and hair.


5 Pharmacology and Biochemistry
5.1 Pharmacology

Castor oil is a potent laxative that was shown to be effective for short-term constipation. In a prospective study, the group receiving oral castor oil was associated with a higher likelihood of initiation of labour compared to the placebo group. Castor oil is known to induce diarrhea, and has been used in studies to assess anti-diarrheal effect of some compounds.


5.2 MeSH Pharmacological Classification

Cathartics

Agents that are used to stimulate evacuation of the bowels. (See all compounds classified as Cathartics.)


5.3 ATC Code

A - Alimentary tract and metabolism

A06 - Drugs for constipation

A06A - Drugs for constipation

A06AB - Contact laxatives

A06AB05 - Castor oil


5.4 Absorption, Distribution and Excretion

Absorption

After oral ingestion of castor oil, ricinoleic acid is released by lipases in the intestinal lumen and absorbed in the intestine. Findings from the rat study suggest that the absorption of castor oil is inversely related to the administered dose, but the absorption is virtually complete at small doses (4g).


Route of Elimination

Fecal recovery of radio-labelled castor oil ranged from 11.4% (for 10 g dose of castor oil) to 86.0% (for 44.4 g dose of castor oil).


Volume of Distribution

No pharmacokinetic data available.


Clearance

No pharmacokinetic data available.


... Some absorption of its intestinal metabolites occurs before the intestine is cleared.

Hayes, W. J., Jr. Toxicology of Pesticides Baltimore: Williams & Wilkins, 1975., p. 397


Ricinoleate, like other anionic surfactants, reduces net absorption of fluid and electrolytes and stimulates intestinal peristalsis. Ricinoleic acid also is absorbed and metabolized like other fatty acids.

Hardman, J.G., L.E. Limbird, P.B. Molinoff, R.W. Ruddon, A.G. Goodman (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 9th ed. New York, NY: McGraw-Hill, 1996., p. 924


Two rabbits (weight = 3 kg) were fed 6% castor oil in the diet for 18 days; fecal collection occurred during the last ten days. The utilization (uncorrected for metabolic fat) of castor oil was 92.1%, which /was/ considered to be efficient utilization. For both rabbits, the percentage of fat in the feces was 2.2%.

Cosmetic Ingredient Review Expert Panel; Int J Toxicol 26 (Suppl. 3): 31-77 (2007)


Adult rats (number, weights, and strain not stated) received a diet containing 48.4% castor oil for 4 to 6 weeks. Control rats received stock ration only. Feces were collected from three rats on the castor oil diet. At the end of the feeding period, excised organs/tissues were ground thoroughly and samples of phospholipid fatty acids were obtained from the liver, small intestine, and muscle; glyceride fatty acids were obtained from the liver and fat depots. There was no evidence of catharsis in any of the animals. Average percentages of Ricinoleic Acid in the phospholipid fatty acids were as follows: liver (test: 1.3 +/- 0.6% [9 analyses]; controls: 1.7 +/- 1.1% [7 analyses]), small intestine (test: 4.9 +/- 1.7% [8 analyses]; controls: 6.0 +/- 4.4% [4 analyses]), and skeletal muscle (test: 3.6 +/- 2.9% [8 analyses]; controls: 4.0 +/- 1.7% [7 analyses]). The following values are average percentages of Ricinoleic Acid in glycerides and cholesterol esters: fat depots (test: 6.8 +/- 4.2% [11 analyses]; controls: 0.5 +/- 0.5% [7 analyses]) and liver (test: 7.2 +/- 2.4% [8 analyses]; controls: 5.6 +/- 4.1% [5 analyses]). /It was/ concluded that the feeding of castor oil did not lead to the appearance of significant amounts of Ricinoleic Acid in phospholipids of the small intestine, liver, and skeletal muscle, nor in glycerides of the liver. Additionally, they concluded that ricinoleic acid is a component acid of the glycerides in the fat depots, comprising 7% of the total fatty acids. The fatty acids excreted by each of three rats amounted to 2.1%, 2.2%, and 3.6% of those ingested. Total body fat in these three animals was also determined, and it was calculated that 1% to 2% of absorbed Ricinoleic Acid was deposited in the fat depots. /It was/ concluded that Ricinoleic Acid was rapidly metabolized.

Cosmetic Ingredient Review Expert Panel; Int J Toxicol 26 (Suppl. 3): 31-77 (2007)


For more Absorption, Distribution and Excretion (Complete) data for Castor oil (7 total), please visit the HSDB record page.


5.5 Metabolism/Metabolites

Castor oil is hydrolyzed to glycerol and ricinoleic acid via pancreatic or intestinal lipase activity. Ricinoleic acid is metabolized systemically and the metabolites are excreted. Fatty acids are expected to be degraded by pancreatic and intestinal lipase.


Castor Oil is a triglyceride that is hydrolyzed in the small intestine in humans by pancreatic enzymes, leading to the release of glycerol and Ricinoleic Acid.

Cosmetic Ingredient Review Expert Panel; Int J Toxicol 26 (Suppl. 3): 31-77 (2007)


Within the small intestine, ... pancreatic lipases hydrolyze the oil to glycerol and ricinoleic acid. Ricinoleate, like other anionic surfactants, reduces net absorption of fluid and electrolytes and stimulates intestinal peristalsis. Ricinoleic acid also is absorbed and metabolized like other fatty acids.

Hardman, J.G., L.E. Limbird, P.B. Molinoff, R.W. Ruddon, A.G. Goodman (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 9th ed. New York, NY: McGraw-Hill, 1996., p. 924


Castor oil was administered intragastrically to germ-free and conventional rats (number not stated). Urine was collected at intervals over a 24-hr period. The following epoxydicarboxylic acids were detected in the urine of both germ-free and conventional rats: 3,6-epoxyoctanedioic acid; 3,6-epoxydecanedioic acid; and 3,6- epoxydodecanedioic acid. These acids were not detected in urine collected from the rats prior to dosing with castor oil, and they also were not detected in steam-sterilized castor oil. Results for the germ-free rat indicate that the cyclization of Ricinoleic Acid (hydroxy fatty acid in castor oil) to form an epoxy compound occurs endogenously and does not require the presence of intestinal bacteria.

Cosmetic Ingredient Review Expert Panel; Int J Toxicol 26 (Suppl. 3): 31-77 (2007)


Castor oil (10 to 15 mL) /was administered/ orally to three healthy subjects. Urine was collected between 2 and 8 hr post dosing. The following three epoxydicarboxylic acids were excreted in the urine: 3,6-epoxyoctanedioic acid; 3,6-epoxydecanedioic acid; and 3,6-epoxydodecanedioic acid.

Cosmetic Ingredient Review Expert Panel; Int J Toxicol 26 (Suppl. 3): 31-77 (2007)


5.6 Biological Half-Life

No pharmacokinetic data available.


5.7 Mechanism of Action

Castor oil is a mix of triglycerides consisting of mainly ricinolein, linoleic acid, oleic acid, palmitic acid, stearic acid, dihydroxystearic acid, and traces of other fatty acids. The main pharmacodynamic effects of castor oil are mediated by ricinoleic acid, a hydroxylated fatty acid released from castor oil by intestinal lipases. It was believed that ricinoleic acid acts as an anionic surfactant that reduces net absorption of fluid and electrolytes, and stimulates intestinal peristalsis. However, a recent study suggests that ricinoleic acid interacts with EP3 prostanoid receptors expressed on intestinal and uterine smooth muscles. Via activating EP3 prostanoid receptors on intestinal and uterine smooth muscle cells, ricinoleic acid promotes laxation and uterus contraction, respectively. EP3 receptor act as the major prostanoid receptor in the intestine mediating propulsive effects on gut motility, and activation of EP3 receptors has been demonstrated to evoke contraction of uterine smooth muscle.


Castor oil has been classified as a stimulant because lipolysis in small intestine liberates ricinoleic acid ... /which/ stimulates smooth muscle and inhibits the absorption of water and electrolytes resulting in fluid accumulation in vitro, but it is not known whether these changes affect fluid movement or...laxative effect in vivo.

American Medical Association, AMA Department of Drugs. AMA Drug Evaluations. 4th ed. Chicago: American Medical Association, 1980., p. 982


In a study involving male Crl:CD BR rats, the findings suggested that castor oil-induced diarrhea is the result of activation of NK1 and NK2 receptors by endogenous tachykinins.

Cosmetic Ingredient Review Expert Panel; Int J Toxicol 26 (Suppl. 3): 31-77 (2007)


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