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Chemistry

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Also known as: 26675-46-7, Forane, 1-chloro-2,2,2-trifluoroethyl difluoromethyl ether, 2-chloro-2-(difluoromethoxy)-1,1,1-trifluoroethane, Forene, Aerrane

Molecular Formula

C₃H₂ClF₅O

Molecular Weight

184.49 g/mol

InChI Key

PIWKPBJCKXDKJR-UHFFFAOYSA-N

FDA UNII

CYS9AKD70P

A stable, non-explosive inhalation anesthetic, relatively free from significant side effects.

Isoflurane is a General Anesthetic. The physiologic effect of isoflurane is by means of General Anesthesia.

1 2D Structure

Isoflurane

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

2-chloro-2-(difluoromethoxy)-1,1,1-trifluoroethane

2.1.2 InChI

InChI=1S/C3H2ClF5O/c4-1(3(7,8)9)10-2(5)6/h1-2H

2.1.3 InChI Key

PIWKPBJCKXDKJR-UHFFFAOYSA-N

2.1.4 Canonical SMILES

C(C(F)(F)F)(OC(F)F)Cl

2.2 Other Identifiers

2.2.1 UNII

CYS9AKD70P

2.3 Synonyms

2.3.1 Depositor-Supplied Synonyms

1. 26675-46-7

2. Forane

3. 1-chloro-2,2,2-trifluoroethyl Difluoromethyl Ether

4. 2-chloro-2-(difluoromethoxy)-1,1,1-trifluoroethane

5. Forene

6. Aerrane

7. Isoflurano

8. Compound 469

9. Isoflo

10. Isofluranum

11. Ethane, 2-chloro-2-(difluoromethoxy)-1,1,1-trifluoro-

12. R-e 235dal

13. Terrell

14. Ether, 1-chloro-2,2,2-trifluoroethyl Difluoromethyl

15. Hsdb 8057

16. Cys9akd70p

17. Compound-469

18. Chebi:6015

19. 2-chloro-2-difluoromethoxy-1,1,1-trifluoroethane

20. Isofluranum [inn-latin]

21. Ncgc00181037-01

22. Aerrane (veterinary)

23. Dsstox_cid_752

24. Dsstox_rid_75769

25. Dsstox_gsid_20752

26. Isoba; Isofor; Isoforine; Isorrane; R-e 235da1

27. Isoflurano [inn-spanish]

28. Difluoromethyl 1-chloro-2,2,2-trifluoroethyl Ether (isoflurane)

29. Cas-26675-46-7

30. Forane (tn)

31. Ccris 3043

32. Isoflurane [anaesthetics, Volatile]

33. Einecs 247-897-7

34. Unii-cys9akd70p

35. Mfcd00066609

36. Brn 1852087

37. (+/-)-isoflurane

38. Isoflurane [usan:usp:inn:ban:jan]

39. Terrellhsdb 8057

40. Compd 469

41. Isoflurane, Aldrichcpr

42. Isoflurane [mi]

43. Isoflurane [inn]

44. Isoflurane [jan]

45. Isoflurane [usan]

46. Isoflurane [vandf]

47. Isoflurane [mart.]

48. Schembl1532

49. Chembl1256

50. Isoflurane [usp-rs]

51. Isoflurane [who-dd]

52. Difluoromethyl 1-chloro-2,2,2-trifluoroethyl Ether

53. Gtpl2505

54. Hsdb8057

55. Isoflurane (jp17/usp/inn)

56. Isoflurane [green Book]

57. Dtxsid3020752

58. Isoflurane [orange Book]

59. Hsdb-8057

60. Isoflurane [ep Monograph]

61. Bdbm217353

62. Isoflurane [usp Monograph]

63. Amy33546

64. Tox21_112685

65. Tox21_200831

66. Bbl100111

67. S6917

68. Stl454337

69. Akos006228574

70. Db00753

71. Ks-5166

72. Pb47772

73. Ncgc00181037-02

74. Ncgc00181037-03

75. Ncgc00258385-01

76. Ac-154802

77. Db-046999

78. Cs-0017450

79. Ft-0627416

80. C07518

81. D00545

82. P15338

83. A818554

84. Q413918

85. Sr-01000944965

86. Sr-01000944965-1

87. W-107162

88. 1-chloro-1-(difluoromethoxy)-2,2,2-trifluoroethane

89. 2-chloro-2-(difluoromethoxy)-1,1,1-trifluoro-ethane

90. 1-chloro-2,2,2-trifluroethyl Difluromethyl Ether

91. Ethane, 1-chloro-1-(difluoromethoxy)-2,2,2-trifluoro-

92. 2-[bis(fluoranyl)methoxy]-2-chloranyl-1,1,1-tris(fluoranyl)ethane

2.4 Create Date

2005-03-25

3 Chemical and Physical Properties

Molecular Formula	C₃H₂ClF₅O
Molecular Weight	184.49 g/mol
XLogP3	2.1
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	2
Exact Mass	183.9714332 g/mol
Monoisotopic Mass	183.9714332 g/mol
Topological Polar Surface Area	9.2 Å²
Heavy Atom Count	10
Formal Charge	0
Complexity	102
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	1
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Information

1 of 4
Drug Name	Forane
Drug Label	FORANE (isoflurane, USP), a nonflammable liquid administered by vaporizing, is a general inhalation anesthetic drug. It is 1-chloro-2, 2,2-trifluoroethyl difluoromethyl ether, and its structural formula is:Some physical constants are:Molecular weight...
Active Ingredient	Isoflurane
Dosage Form	Liquid
Route	Inhalation
Strength	99.9%
Market Status	Prescription
Company	Baxter Hlthcare

2 of 4
Drug Name	Isoflurane
Drug Label	Isoflurane, USP, is a nonflammable, nonexplosive general inhalation anesthetic agent. Its chemical name is 1-chloro-2,2,2-trifluoroethyl difluoromethyl ether, and its structural formula is:Each mL contains 99.9% Isoflurane.Some physical const...
Active Ingredient	Isoflurane
Dosage Form	Liquid
Route	Inhalation
Strength	99.9%
Market Status	Prescription
Company	Hospira; Halocarbon Prods; Piramal Critical; Piramal Ent

3 of 4
Drug Name	Forane
Drug Label	FORANE (isoflurane, USP), a nonflammable liquid administered by vaporizing, is a general inhalation anesthetic drug. It is 1-chloro-2, 2,2-trifluoroethyl difluoromethyl ether, and its structural formula is:Some physical constants are:Molecular weight...
Active Ingredient	Isoflurane
Dosage Form	Liquid
Route	Inhalation
Strength	99.9%
Market Status	Prescription
Company	Baxter Hlthcare

4 of 4
Drug Name	Isoflurane
Drug Label	Isoflurane, USP, is a nonflammable, nonexplosive general inhalation anesthetic agent. Its chemical name is 1-chloro-2,2,2-trifluoroethyl difluoromethyl ether, and its structural formula is:Each mL contains 99.9% Isoflurane.Some physical const...
Active Ingredient	Isoflurane
Dosage Form	Liquid
Route	Inhalation
Strength	99.9%
Market Status	Prescription
Company	Hospira; Halocarbon Prods; Piramal Critical; Piramal Ent

4.2 Therapeutic Uses

FORANE (isoflurane, USP) may be used for induction and maintenance of general anesthesia. Adequate data have not been developed to establish its application in obstetrical anesthesia.

US Natl Inst Health; DailyMed. Current Medication Information for Forane (isoflurane) inhalant (December 2011). Available from, as of July 23, 2012: https://dailymed.nlm.nih.gov/dailymed/lookup.cfm?setid=3d30eb8d-a62e-475f-926b-78ba63bee9c8

In cases of life-threatening status asthmaticus which are refractory to drug therapy, the administration of inhalation anesthetics can be life-saving as they help alleviate bronchial spasm. We had an 11-year-old female patient suffering from status asthmaticus who was moribund from severe CO2 narcosis and was not responding to any of the conventional therapies. She finally fell into ventricular fibrillation. After cardiopulmonary resuscitation, we administered 2.0% isoflurane in oxygen. Within half an hour, her high inspiratory pressure was dramatically decreased, and then the isoflurane concentration was maintained at 1.0%. After 14 hours of isoflurane anesthesia, PaCO2 decreased to the normal level and the isoflurane treatment was discontinued. The endotracheal tube was removed 4 hours later. She had an uneventful recovery and was discharged from the hospital 11 days later. With its low metabolic rate and therefore low organ toxicity, as well as its low arrhythmogenicity with remarkable bronchodilating activity, we feel isoflurane may well be superior to other inhalation anesthetics in the treatment of status asthmaticus.

PMID:8433481 Shibata Y et al; Masui 42 (1): 116-9 (1993)

Vet: Isoflurane, USP is used for induction and maintenance of general anesthesia in horses and dogs.

US Natl Inst Health; DailyMed. Current Medication Information for Isoflurane USP (isoflurane) inhalant (August 2009). Available from, as of July 23, 2012: https://dailymed.nlm.nih.gov/dailymed/lookup.cfm?setid=b0c8964f-24a8-4bab-ae8d-1536737e43ec

4.3 Drug Warning

Anesthetics, Inhalation

National Library of Medicine's Medical Subject Headings online file (MeSH, 2009) https://www.nlm.nih.gov/cgi/mesh/2012/MB_cgi?mode=&term=Isoflurane

In susceptible individuals, isoflurane anesthesia may trigger a skeletal muscle hypermetabolic state leading to high oxygen demand and the clinical syndrome known as malignant hyperthermia. The syndrome includes nonspecific features such as muscle rigidity, tachycardia, tachypnea, cyanosis, arrhythmias, and unstable blood pressure. (It should also be noted that many of these nonspecific signs may appear with light anesthesia, acute hypoxia, etc.) An increase in overall metabolism may be reflected in an elevated temperature, (which may rise rapidly early or late in the case, but usually is not the first sign of augmented metabolism) and an increased usage of the CO2 absorption system (hot canister). PaO2 and pH may decrease, and hyperkalemia and a base deficit may appear.

Since levels of anesthesia may be altered easily and rapidly, only vaporizers producing predictable concentrations should be used. Hypotension and respiratory depression increase as anesthesia is deepened.

Increased blood loss comparable to that seen with halothane has been observed in patients undergoing abortions.

For more Drug Warnings (Complete) data for Isoflurane (24 total), please visit the HSDB record page.

4.4 Drug Indication

For induction and maintenance of general anesthesia.

FDA Label

Sedation of mechanically ventilated patients

5 Pharmacology and Biochemistry

5.1 Pharmacology

Isoflurane is a general inhalation anesthetic used for induction and maintenance of general anesthesia. It induces muscle relaxation and reduces pains sensitivity by altering tissue excitability. It does so by decreasing the extent of gap junction mediated cell-cell coupling and altering the activity of the channels that underlie the action potential.

5.2 MeSH Pharmacological Classification

Anesthetics, Inhalation

Gases or volatile liquids that vary in the rate at which they induce anesthesia; potency; the degree of circulation, respiratory, or neuromuscular depression they produce; and analgesic effects. Inhalation anesthetics have advantages over intravenous agents in that the depth of anesthesia can be changed rapidly by altering the inhaled concentration. Because of their rapid elimination, any postoperative respiratory depression is of relatively short duration. (From AMA Drug Evaluations Annual, 1994, p173) (See all compounds classified as Anesthetics, Inhalation.)

5.3 FDA Pharmacological Classification

5.3.1 Active Moiety

ISOFLURANE

5.3.2 FDA UNII

CYS9AKD70P

5.3.3 Pharmacological Classes

General Anesthetic [EPC]; General Anesthesia [PE]

5.4 ATC Code

N - Nervous system

N01 - Anesthetics

N01A - Anesthetics, general

N01AB - Halogenated hydrocarbons

N01AB06 - Isoflurane

5.5 Absorption, Distribution and Excretion

In the postanesthesia period, only 0.17% of the isoflurane taken up can be recovered as urinary metabolites.

It is not known whether this drug is excreted in human milk.

5.6 Metabolism/Metabolites

Minimal

Renal and hepatic toxicity of the fluorinated ether volatile anesthetics is caused by biotransformation to toxic metabolites. Metabolism also contributes significantly to the elimination pharmacokinetics of some volatile agents. Although innumerable studies have explored anesthetic metabolism in animals, there is little information on human volatile anesthetic metabolism with respect to comparative rates or the identity of the enzymes responsible for defluorination. The first purpose of this investigation was to compare the metabolism of the fluorinated ether anesthetics by human liver microsomes. The second purpose was to test the hypothesis that cytochrome P450 2E1 is the specific P450 isoform responsible for volatile anesthetic defluorination in humans. Microsomes were prepared from human livers. Anesthetic metabolism in microsomal incubations was measured by fluoride production. The strategy for evaluating the role of P450 2E1 in anesthetic defluorination involved three approaches: for a series of 12 human livers, correlation of microsomal defluorination rate with microsomal P450 2E1 content (measured by Western blot analysis), correlation of defluorination rate with microsomal P450 2E1 catalytic activity using marker substrates (para-nitrophenol hydroxylation and chlorzoxazone 6-hydroxylation), and chemical inhibition by P450 isoform-selective inhibitors. The rank order of anesthetic metabolism, assessed by fluoride production at saturating substrate concentrations, was methoxyflurane > sevoflurane > enflurane > isoflurane > desflurane > 0. There was a significant linear correlation of sevoflurane and methoxyflurane defluorination with antigenic P450 2E1 content (r = 0.98 and r = 0.72, respectively), but not with either P450 1A2 or P450 3A3/4. Comparison of anesthetic defluorination with either para-nitrophenol or chlorzoxazone hydroxylation showed a significant correlation for sevoflurane (r = 0.93, r = 0.95) and methoxyflurane (r = 0.78, r = 0.66). Sevoflurane defluorination was also highly correlated with that of enflurane (r = 0.93), which is known to be metabolized by human P450 2E1. Diethyldithiocarbamate, a selective inhibitor of P450 2E1, produced a concentration-dependent inhibition of sevoflurane, methoxyflurane, and isoflurane defluorination. No other isoform-selective inhibitor diminished the defluorination of sevoflurane, whereas methoxyflurane defluorination was inhibited by the selective P450 inhibitors furafylline (P450 1A2), sulfaphenazole (P450 2C9/10), and quinidine (P450 2D6) but to a much lesser extent than by diethyldithiocarbamate. These results demonstrate that cytochrome P450 2E1 is the principal, if not sole human liver microsomal enzyme catalyzing the defluorination of sevoflurane. P450 2E1 is the principal, but not exclusive enzyme responsible for the metabolism of methoxyflurane, which also appears to be catalyzed by P450s 1A2, 2C9/10, and 2D6. The data also suggest that P450 2E1 is responsible for a significant fraction of isoflurane metabolism. Identification of P450 2E1 as the major anesthetic metabolizing enzyme in humans provides a mechanistic understanding of clinical fluorinated ether anesthetic metabolism and toxicity.

PMID:8214760 Kharasch ED, Thummel KE; Anesthesiology 79 (4): 795-807 (1993)

Isoflurane undergoes minimal biotransformation in man.

PMID:8214760 Kharasch ED, Thummel KE; Anesthesiology 79 (4): 795-807 (1993)

5.7 Mechanism of Action

Isoflurane induces a reduction in junctional conductance by decreasing gap junction channel opening times and increasing gap junction channel closing times. Isoflurane also activates calcium dependent ATPase in the sarcoplasmic reticulum by increasing the fluidity of the lipid membrane. Also appears to bind the D subunit of ATP synthase and NADH dehydogenase. Isoflurane also binds to the GABA receptor, the large conductance Ca²⁺ activated potassium channel, the glutamate receptor and the glycine receptor.

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Aesica Queenborough Ltd

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Shandong New Time Pharmaceutical Co ...

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Shandong New Time Pharmaceutical Co ...

China

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Piramal Pharma Ltd

India

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Great Lakes Chemical Corp

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Great Lakes Chemical Corp

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AbbVie Inc. North Chicago US

U.S.A

AES 2024

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Isoflurane

Certificate Number : R1-CEP 2006-292 - Rev 00

Status : Valid

Issue Date : 2012-09-24

Type : Chemical

Substance Number : 1673

Product Web Link

Corporate PDF

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AESICA QUEENBOROUGH LIMITED Queenbo...

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China

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Piramal Pharma Solutions

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Rochem International Inc

U.S.A

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Isoflurane

About the Company : Established in 1994, Rochem is a distributor of pharmaceutical, food, nutritional and animal health ingredients to some of the largest companies in the world. It sources high-quali...

Established in 1994, Rochem is a distributor of pharmaceutical, food, nutritional and animal health ingredients to some of the largest companies in the world. It sources high-quality ingredients manufactured in China. Headquartered in the Hauppauge, New York, Rochem has 16 offices spread across the globe to cater to the needs of its customers. Rochem’s operations are fully cGMP compliant and has been audited by the USFDA as well as several multinational organizations. It also trains and audits its partners to ensure all of their technologies and systems are FDA-compliant.

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Suanfarma

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Isoflurane

About the Company : Suanfarma founded in 1993, is a B2B life science partner committed to health & innovation by developing, manufacturing, & distributing high-quality APIs for the pharmaceutical indu...

Suanfarma founded in 1993, is a B2B life science partner committed to health & innovation by developing, manufacturing, & distributing high-quality APIs for the pharmaceutical industry innovatively & sustainably. Backed by a robust global network of 12 strategically located local offices, we cater to the needs of over 400 active customers in 70+ countries. At Suanfarma we offer our CDMO capacity for fermentation & chemical synthesis projects, offering a One Stop Shop service with a solid track record, & which allows us to achieve success in the development, scaling, manufacturing, & commercialization of an API, either innovative or generic.

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Hebei AiYoung Pharmaceutical Techno...

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Lunan Pharmaceutical

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API Reference Price

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