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Chemistry

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Also known as: 110-27-0, Isopropyl tetradecanoate, Tetradecanoic acid, 1-methylethyl ester, Estergel, Bisomel, Isomyst
Molecular Formula
C17H34O2
Molecular Weight
270.5  g/mol
InChI Key
AXISYYRBXTVTFY-UHFFFAOYSA-N
FDA UNII
0RE8K4LNJS

Isopropyl Myristate API
isopropyl myristate is a natural product found in Siraitia grosvenorii with data available.
1 2D Structure

Isopropyl Myristate API

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
propan-2-yl tetradecanoate
2.1.2 InChI
InChI=1S/C17H34O2/c1-4-5-6-7-8-9-10-11-12-13-14-15-17(18)19-16(2)3/h16H,4-15H2,1-3H3
2.1.3 InChI Key
AXISYYRBXTVTFY-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CCCCCCCCCCCCCC(=O)OC(C)C
2.2 Other Identifiers
2.2.1 UNII
0RE8K4LNJS
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Isopropylmyristate

2.3.2 Depositor-Supplied Synonyms

1. 110-27-0

2. Isopropyl Tetradecanoate

3. Tetradecanoic Acid, 1-methylethyl Ester

4. Estergel

5. Bisomel

6. Isomyst

7. Promyr

8. Deltyl Extra

9. Kesscomir

10. Tegester

11. Wickenol 101

12. Sinnoester Mip

13. Crodamol Ipm

14. Plymoutm Ipm

15. Stepan D-50

16. Propan-2-yl Tetradecanoate

17. Starfol Ipm

18. Unimate Ipm

19. Kessco Ipm

20. Emcol-im

21. Myristic Acid Isopropyl Ester

22. Emerest 2314

23. 1-methylethyl Tetradecanoate

24. Ja-fa Ipm

25. Fema No. 3556

26. Kessco Isopropyl Myristate

27. Crodamol I.p.m.

28. Tetradecanoic Acid, Isopropyl

29. Myristic Acid, Isopropyl Ester

30. Isopropyl Myristate [usan]

31. Tetradecanoic Acid, Isopropyl Ester

32. Hsdb 626

33. Nsc 406280

34. 1-tridecanecarboxylic Acid, Isopropyl Ester

35. Isopropyl Tetradecanoic Acid

36. Estergel (tn)

37. Methylethyl Tetradecanoate

38. 0re8k4lnjs

39. Iso-propyl N-tetradecanoate

40. Nsc-406280

41. Chebi:90027

42. Tetradecanoic Acid Methyethyl Ester

43. 1405-98-7

44. Ncgc00164071-01

45. Deltylextra

46. We(2:0(1me)/14:0)

47. Dsstox_cid_6838

48. Isopropyl Myristate, 98%

49. Dsstox_rid_78224

50. Dsstox_gsid_26838

51. Caswell No. 511e

52. Cas-110-27-0

53. Einecs 203-751-4

54. Unii-0re8k4lnjs

55. Mfcd00008982

56. Epa Pesticide Chemical Code 000207

57. Brn 1781127

58. Tegosoft M

59. Isopropyl Myristate [usan:nf]

60. Liponate Ipm

61. Crodamol 1pm

62. Isopropyl-myristate

63. Lexol Ipm

64. Isopropyltetradecanoate

65. Myristic Acid Isopropyl

66. Radia 7190

67. Isopropyl Myristate (nf)

68. Ec 203-751-4

69. Schembl2442

70. Component Of Sardo Bath Oil

71. Myristic Acid-isopropyl Ester

72. Isopropyl Myristate, >=98%

73. Chembl207602

74. Ipm 90

75. Dtxsid0026838

76. Isopropyl Myristate [ii]

77. Isopropyl Myristate [mi]

78. Wln: 13voy1&1

79. Fema 3556

80. Tetradecanoic Acid Isopropyl Ester

81. Isopropyl Myristate [fhfi]

82. Isopropyl Myristate [hsdb]

83. Isopropyl Myristate [inci]

84. Isopropyl Myristate [vandf]

85. Isopropyl Myristate [mart.]

86. Zinc8214588

87. Isopropyl Myristate, >=90% (gc)

88. Tox21_112080

89. Tox21_202065

90. Tox21_303171

91. Isopropyl Myristate [usp-rs]

92. Isopropyl Myristate [who-dd]

93. Lmfa07010677

94. Nsc406280

95. S2428

96. Akos015902296

97. Tox21_112080_1

98. Db13966

99. Component Of Sardo Bath Oil (salt/mix)

100. Ncgc00164071-02

101. Ncgc00164071-03

102. Ncgc00256937-01

103. Ncgc00259614-01

104. Isopropyl Myristate [ep Monograph]

105. Ls-14615

106. Db-040910

107. Hy-124190

108. Cs-0085813

109. Ft-0629053

110. M0481

111. Myristic Acid, Isopropyl Alcohol Ester

112. D02296

113. F71211

114. Tetradeconoic Acid, 1-methylethyl Ester

115. Q416222

116. Sr-01000944751

117. Isopropyl Myristate, Vetec(tm) Reagent Grade, 98%

118. Q-201418

119. Sr-01000944751-1

120. Isopropyl Myristate, United States Pharmacopeia (usp) Reference Standard

121. Tetradecanoic Acid,isopropyl Ester (myristate,isopropyl Ester)

122. Isopropyl Myristate, Pharmaceutical Secondary Standard; Certified Reference Material

2.4 Create Date
2005-03-26
3 Chemical and Physical Properties
Molecular Weight 270.5 g/mol
Molecular Formula C17H34O2
XLogP37.2
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count2
Rotatable Bond Count14
Exact Mass270.255880323 g/mol
Monoisotopic Mass270.255880323 g/mol
Topological Polar Surface Area26.3 Ų
Heavy Atom Count19
Formal Charge0
Complexity199
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Therapeutic Uses

... Isopropyl myristate 50% in cyclomethicone solution (Full Marks Solution - SSL International) is a new fluid treatment with a physical mode of action that uses a 10-minute contact time /for treatment of head lice.

PMID:19423676 Drug Ther Bull 47 (5): 50-2 (2009) (No authors given)


/Experimental Therapy/ ... A pediculicide rinse, 50% isopropyl myristate (IPM), was assessed in two phase 2 trials conducted in North America. The first trial was a nonrandomized (proof of concept) trial without a comparator conducted in Winnipeg, Canada. The second trial, conducted in the United States, was an evaluator-blinded, randomized superiority trial comparing 50% IPM rinse with a positive control (RID; pyrethrin 0.33%, piperonyl butoxide 4%). The primary end points were to determine the safety and efficacy of 50% IPM as a pediculicide rinse. METHODS: Subjects meeting inclusion criteria were enrolled in the above-mentioned trials with efficacy end points 7 and 14 days post-treatment. Subjects were also evaluated on days 0, 7, 14, and 21 for the presence of erythema and edema using the Modified Draize Scale. Other comments associated with the safety evaluation (ie, pruritus) were collected. RESULTS: IPM was found to be effective in the proof of concept study and comparator trial using a positive control. IPM was also well tolerated, with minimal adverse events. All adverse events were mild, resolving by completion of the study. CONCLUSION: Data suggest that IPM is a safe and effective therapy for the treatment of head lice in children and adults. IPM's mechanical mechanism of action makes development of lice resistance unlikely.

PMID:17942025 Kaul N et al; J Cutan Med Surg 11 (5): 161-7 (2007)


... Due to their distinct advantages such as enhanced drug solubility, thermodynamic stability, facile preparation, and low cost, uses and applications of microemulsions have been numerous. Recently, there is a surge in the exploration of microemulsion for transdermal drug delivery for their ability to incorporate both hydrophilic (5-fluorouracil, apomorphine hydrochloride, diphenhydramine hydrochloride, tetracaine hydrochloride, and methotrexate) and lipophilic drugs (estradiol, finasteride, ketoprofen, meloxicam, felodipine, and triptolide) and enhance their permeation.... Besides surfactants, oils can also act as penetration enhancers (oleic acid, linoleic acid, isopropyl myristate, isopropyl palmitate, etc.). ...

PMID:19016057 Azeem A et al; Drug Dev Ind Pharm 35 (5): 525-47(2009)


/Experimental Therapy/ Alpha-tocopherol (AT) is the vitamin E homologue with the highest in vivo biological activity. AT protects against the carcinogenic and mutagenic activity of ionizing radiation and chemical agents, and possibly against UV-induced cutaneous damage. For stability consideration, alpha-tocopherol is usually used as its prodrug ester, alpha-tocopherol acetate (ATA), which once absorbed into the skin is hydrolyzed to alpha-tocopherol, the active form. ... Permeation studies were conducted using modified Franz diffusion cells and human cadaver skin as the membrane. Specifically, 5% (w/w) alpha-tocopherol acetate was formulated in the following vehicles: ethanol, isopropyl myristate, light mineral oil, 1% Klucel gel in ethanol, and 3% Klucel gel in ethanol (w/w). ... The permeabilities of ATA through human cadaver skin were 1.0x10-4, 1.1x10-2, 1.4x10-4, 2.1x10-4, and 4.7x10-4 cm/hr for the ethanol solution, isopropyl myristate solution, light mineral oil solution, 1% Klucel gel, and 3% Klucel gel, respectively. The results show that the formulation had relatively minor effects on the permeability coefficients of ATA through cadaver skin in all cases except for the isopropyl myristate solution.

PMID:15868062 Mahamongkol H et al; J Cosmet Sci 56 (2): 91-103 (2005)


For more Therapeutic Uses (Complete) data for Isopropyl myristate (7 total), please visit the HSDB record page.


4.2 Drug Warning

One must, however, look carefully for an intensification of possible risks related to the method of application, the condition of the skin, the site of application, supporting therapeutic measures or changes in the composition of the vehicle. Lanolin, cetyl alcohol and myristyl alcohol, sorbitol, isopropyl-myristate as well as polyethylene glycols (PEG) penetrate the skin like active substances...

PMID:2971521 Zesch A; Derm Beruf Umwelt 36 (4): 128-33 (1988)


Many enhancers are concentration-dependent; therefore, optimal concentration for effective promotion should be determined. The delivery rate is dependent on the type of the drug, the structure and ingredients of the carrier, and on the character of the membrane in use. Each formulation should be examined very carefully, because every membrane alters the mechanism of penetration and can turn an enhancer to a retarder.

PMID:16843424 Kogan A, Garti N; Adv Colloid Interface Sci 123-6: 369-85 (2006)


Cosmetics continue to be used by acne-prone individuals. ... The data presented were gleaned from the rabbit ear assay, which is not an ideal animal model but is the best we have. If an ingredient is negative in the rabbit ear assay, we feel it is safe on the acne-prone skin. A strong, positive ingredient or cosmetic should be avoided. Ingredient offenders include isopropyl myristate and its analogs, such as isopropyl palmitate, isopropyl isostearate, butyl stearate, isostearyl neopentanoate, myristyl myristate, decyl oleate, octyl stearate, octyl palmitate or isocetyl stearate, and new introductions by the cosmetic industry, such as propylene glycol-2 (PPG-2) myristyl propionate...

PMID:6229554 Fulton JE Jr et al; J Am Acad Dermatol 10 (1): 96-105 (1984)


... How the alternative use of three lipophilic excipients ... , differing in their polarity indexes (medium chain triglycerides (MG), decyl oleate (DO), and isopropyl myristate (IPM), respectively), affects the colloidal structure of the alkylpolyglucoside-based vehicles and in vitro permeation profiles of two model drugs: diclofenac sodium (DC) and caffeine (CF), both sparingly soluble in water /were investigated/ . ... Varying of lipophilic excipient influenced noteworthy variations in the colloidal structure demonstrated as different rheological profiles accompanied to the certain degree by different water distribution modes, but notably provoked by drug nature (an amphiphilic electrolyte drug vs. nonelectrolyte). In vitro permeation data obtained using ASC membranes in an infinite dose-type of experiment stressed the importance of the vehicle/solute interactions in case of small variation in formulation composition, asserting the drug properties in the first hours of permeation and rheological profile of the vehicles in the later phase of experiment as decisive factors...

PMID:19616085 Savic S et al; Int J Pharm 381 (2): 220-30 (2009)


4.3 Drug Indication

The primary medical indication for which isopropyl myristate is formally used as an active ingredient in a patient care product is as a non-prescription pediculicide rinse.


FDA Label


5 Pharmacology and Biochemistry
5.1 Pharmacology

Isopropyl myristate is an emollient vehicle that is effective at enhancing the penetration of other medical agents that may be incorporated into the vehicle as active agents. In one study, a 50:50 isopropanol-isopropyl myristate binary enhancer synergistically increased the transport of estradiol across a two-layer human epidermis in vitro.


5.2 Absorption, Distribution and Excretion

Absorption

Dermal absorption of isopropyl myristate is predicated to be 0.00020 mg/cm2/event, which is considered a very low absorption rate. In a study, topically applied isopropyl myristate was largely retained in the stratum corneum. It was not detected in the receptor fluid of flow-through diffusion cells in in-vitro skin permeation experiments using human epidermis (stratum corneum and viable epidermis) and dermis of varying thickness.


Route of Elimination

Readily available information regarding the pharmacokinetics of isopropyl myristate is not available.


Volume of Distribution

Readily available information regarding the pharmacokinetics of isopropyl myristate is not available.


Clearance

Readily available information regarding the pharmacokinetics of isopropyl myristate is not available.


Four monkeys were exposed for 5 sec to the spray of an aerosol antiperspirant containing 14C-labelled isopropyl myristate. Two animals were sacrificed immediately after exposureand the other two were sacrificed 24 hr later. The distribution of carbon-14 in the exhaled air and in several tissues indicated that only 0.25% of the dose sprayed at the animals was absorbed; about 10% of this reached the lower respiratory tract. Some 85% of the absorbed isopropyl myristate was eliminated in 24 hr, mainly as exhaled carbon dioxide; very little labeled material reached any tissues other than the lungs.

Christian M, ed; J American College of Toxicology 1 (4): 55-80 (1982)


In whole body autoradiography in hairless mice, there was no visible penetration into the skin or organs, whereas microautoradipgraphy with guinea pigs showed local penetration. Isopropyl myristate penetrated to the greatest extent. Percutaneous absorption was examined in Angora rabbits by microautoradiography simultaneously with skin irritation potential by histological method. Isopropyl myristate was distributed into the skin both trans-epidermally and trans-follicularly immediately after 24 hr application. Isopropyl myristate is thought to penetrate into human skin also, though it is known to generate no erythema on the skin. Isopropyl myristate was found to be distributed into almost all organs by means of whole body autoradiography when it was injected sc into mice. The extracts from the liver and kidney were determined to be a fatty acid and a triglyceride. Isopropyl myristate was easily distributed into the organs and metabolized.

European Commission, ESIS; IUCLID Dataset, Isopropyl Myristate (110-27-0) p.48 (2000 CD-ROM edition). Available from, as of May 12, 2010: https://esis.jrc.ec.europa.eu/


5.3 Metabolism/Metabolites

Any isopropyl myristate that is absorbed is likely to be hydrolyzed to its component compounds of isopropylalcohol and myristic acid.


The myristates can be expected to undergo chemical or enzymatic hydrolysis to myristic acid and the corresponding alcohol.

Christian M, ed; J American College of Toxicology 1 (4): 55-80 (1982)


Like other high molecular weight aliphatic esters, the myristates are readily hydrolyzed to the corresponding alcohols and acids which are then further metabolized.

Christian M, ed; J American College of Toxicology 1 (4): 55-80 (1982)


5.4 Biological Half-Life

Readily available information regarding the pharmacokinetics of isopropyl myristate is not available.


5.5 Mechanism of Action

As a pediculicide, isopropyl myristate is capable of physically coating the exoskeleton bodies of lice. This physical coating subsequently immobilizes the lice and works to dissolve the wax covering on the insect exoskeleton and blocks the insects' airways, leading to death by dehydration. Although this physical action of isopropyl myristate results in little lice resistance (given the lack of immunologic or chemical activity in this mechanism of action), the substance is also not ovicidal, which means any eggs that may have been laid by lice would not be affected. Moreover, isopropyl myristate is capable of eliciting its pediculicide action in a contact time of only 10 minutes per each necessary administration.


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