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Chemistry

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Also known as: 13647-35-3, Modrenal, Vetoryl, Desopan, Modrastane, Trilostanum
Molecular Formula
C20H27NO3
Molecular Weight
329.4  g/mol
InChI Key
KVJXBPDAXMEYOA-CXANFOAXSA-N
FDA UNII
L0FPV48Q5R

Trilostane
Trilostane is a synthetic derivative of androstane with adrenocortical suppressive properties. Trilostane reversibly inhibits 3 beta-hydroxysteroid dehydrogenase delta 5-4 isomerase in the adrenal cortex, resulting in the decreased synthesis of mineralocorticoids and glucocorticoids and the decreased conversion of pregnenolone to progesterone. (NCI04)
1 2D Structure

Trilostane

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(1S,2R,6R,8S,11S,12S,15S,16S)-5,15-dihydroxy-2,16-dimethyl-7-oxapentacyclo[9.7.0.02,8.06,8.012,16]octadec-4-ene-4-carbonitrile
2.1.2 InChI
InChI=1S/C20H27NO3/c1-18-7-6-14-12(13(18)3-4-15(18)22)5-8-20-17(24-20)16(23)11(10-21)9-19(14,20)2/h12-15,17,22-23H,3-9H2,1-2H3/t12-,13-,14-,15-,17+,18-,19+,20+/m0/s1
2.1.3 InChI Key
KVJXBPDAXMEYOA-CXANFOAXSA-N
2.1.4 Canonical SMILES
CC12CCC3C(C1CCC2O)CCC45C3(CC(=C(C4O5)O)C#N)C
2.1.5 Isomeric SMILES
C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2O)CC[C@]45[C@@]3(CC(=C([C@H]4O5)O)C#N)C
2.2 Other Identifiers
2.2.1 UNII
L0FPV48Q5R
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 4alpha,5-epoxy-17beta-hydroxy-3-oxoandrostane-2-carbonitrile

2. Modrenal

3. Win 24,540

2.3.2 Depositor-Supplied Synonyms

1. 13647-35-3

2. Modrenal

3. Vetoryl

4. Desopan

5. Modrastane

6. Trilostanum

7. Trilostano

8. Win-24540

9. Win 24,540

10. Chebi:32260

11. L0fpv48q5r

12. Win 24540

13. Androst-2-ene-2-carbonitrile, 4,5-epoxy-3,17-dihydroxy-, (4alpha,5alpha,17beta)-

14. Nsc-758904

15. Dsstox_cid_3706

16. Androst-2-ene-2-carbonitrile, 4,5-epoxy-3,17-dihydroxy-, (4a,5a,17b)-

17. Dsstox_rid_77157

18. Dsstox_gsid_23706

19. (1ar,4ar,4bs,6as,7s,9as,9bs,11as)-2,7-dihydroxy-4a,6a-dimethyl-1a,4,4a,4b,5,6,6a,7,8,9,9a,9b,10,11-tetradecahydrocyclopenta[7,8]phenanthro[1,10a-b]oxirene-3-carbonitrile

20. (1s,2r,6r,8s,11s,12s,15s,16s)-5,15-dihydroxy-2,16-dimethyl-7-oxapentacyclo[9.7.0.0^{2,8}.0^{6,8}.0^{12,16}]octadec-4-ene-4-carbonitrile

21. Modrenal (tn)

22. (1ar,4ar,4bs,6as,7s,9as,9bs,11as)-2,7-dihydroxy-4a,6a-dimethyl-1a,4,4a,4b,5,6,6a,7,8,9,9a,9b,10,11-tetradecahydrocyclopenta[7,8]phenanthro[1,10a-b]oxirene-3-carbonitrile.

23. (1s,2r,6r,8s,11s,12s,15s,16s)-5,15-dihydroxy-2,16-dimethyl-7-oxapentacyclo[9.7.0.02,8.06,8.012,16]octadec-4-ene-4-carbonitrile

24. Desopan (tn)

25. Cas-13647-35-3

26. Trilostane (jan/usan)

27. Trilostanum [inn-latin]

28. Trilostano [inn-spanish]

29. Unii-l0fpv48q5r

30. Androst-2-ene-2-carbonitrile, 4,5-epoxy-3,17-dihydroxy-, (4.alpha.,5.alpha.,17.beta.)-

31. Trilostane [usan:inn:ban:jan]

32. Ncgc00274061-01

33. Einecs 237-133-0

34. Mfcd00199295

35. Win 24450

36. Trilostane [mi]

37. Trilostane [inn]

38. Trilostane [jan]

39. Trilostane [usan]

40. Trilostane [vandf]

41. (4alpha,5alpha,17beta)-3,17-dihydroxy-4,5-epoxyandrost-2-ene-2-carbonitrile

42. Schembl7517

43. Trilostane [mart.]

44. Trilostane [who-dd]

45. Gtpl6850

46. Trilostane [green Book]

47. Chembl1200907

48. Dtxsid9023706

49. Trilostane [orange Book]

50. Trilostane, >=98% (hplc)

51. 4.alpha.,5-epoxy-3,17.beta.-dihydroxy-5.alpha.-androst-2-ene-2-carbonitrile

52. Hms3884a15

53. Bcp04132

54. Tox21_112454

55. Tox21_302406

56. 4-alpha,5-epoxy-3,17-dihydroxy-5-alpha-androst-2-ene-2-carbonitrile

57. Ac-927

58. Bdbm50247882

59. S1404

60. 3,17beta-dihydroxy-4alpha,5-epoxy-5alpha-androst-2-ene-2-carbonitrile

61. 4alpha,5-epoxy-3,17beta-dihydroxy-5alpha-androst-2-ene-2-carbonitrile

62. Akos015964043

63. Akos032947221

64. Tox21_112454_1

65. Zinc100038546

66. Ccg-267803

67. Cs-1707

68. Db01108

69. Ks-1414

70. Nsc 758904

71. (2-alpha,4-alpha,5-alpha,17-beta)-4,5-epoxy-17-hydroxy-3-oxoandrostane-2-carbonitrile

72. 4-alpha-5-epoxy-17-beta-hydroxy-3-oxo-5-alpha-androstane-2-alpha-carbonitrile

73. Androstane-2-carbonitrile, 4,5-epoxy-17-hydroxy-3-oxo-, (2-alpha,4-alpha,5-alpha,17-beta)-

74. Ncgc00255201-01

75. Hy-14281

76. Bcp0726000098

77. D01180

78. Ab01274788-01

79. Ab01274788_02

80. 647t353

81. A886681

82. Q907313

83. Q-201884

84. Z1563146079

85. Trilostane; 13647-35-3; Vetoryl; Modrenal; Modrastane

86. (4a,5a,17b)-3,17-dihydroxy-4,5-epoxyandrost-2-ene-2-carbonitrile

87. 5-alpha-androstane-2-alpha-carbonitrile, 4-alpha,5-epoxy-17-beta-hydroxy-3-oxo-

2.4 Create Date
2005-06-24
3 Chemical and Physical Properties
Molecular Weight 329.4 g/mol
Molecular Formula C20H27NO3
XLogP32.9
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count4
Rotatable Bond Count0
Exact Mass329.19909372 g/mol
Monoisotopic Mass329.19909372 g/mol
Topological Polar Surface Area76.8 Ų
Heavy Atom Count24
Formal Charge0
Complexity692
Isotope Atom Count0
Defined Atom Stereocenter Count8
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Indication

Used in the treatment of Cushing's syndrome. It is normally used in short-term treatment until permanent therapy is possible.


5 Pharmacology and Biochemistry
5.1 Pharmacology

Trilostane blocks an enzyme involved in the production of several steroids including cortisol. Inhibiting this enzyme inhibits the production of cortisol. In Cushing's syndrome, the adrenal gland overproduces steroids. Although steroids are important for various functions of the body, too much can cause problems. Trilostane reduces the amount of steroids produced by the adrenal gland. This product was withdrawn from the U.S. market in April 1994.


5.2 MeSH Pharmacological Classification

Abortifacient Agents, Steroidal

Steroidal compounds with abortifacient activity. (See all compounds classified as Abortifacient Agents, Steroidal.)


Antineoplastic Agents

Substances that inhibit or prevent the proliferation of NEOPLASMS. (See all compounds classified as Antineoplastic Agents.)


Enzyme Inhibitors

Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. (See all compounds classified as Enzyme Inhibitors.)


5.3 ATC Code

H - Systemic hormonal preparations, excl. sex hormones and insulins

H02 - Corticosteroids for systemic use

H02C - Antiadrenal preparations

H02CA - Anticorticosteroids

H02CA01 - Trilostane


5.4 Metabolism/Metabolites

Hepatic.


5.5 Biological Half-Life

8 hours.


5.6 Mechanism of Action

Trilostane produces suppression of the adrenal cortex by inhibiting enzymatic conversion of steroids by 3-beta-hydroxysteroid dehydrogenase/delta 5,4 ketosteroid isomerase, thus blocking synthesis of adrenal steroids.


USDMF

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01

Orgamol Sa

Switzerland

USDMF

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Not Confirmed

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Orgamol Sa

Switzerland
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Not Confirmed

GDUFA

DMF Review : N/A

Rev. Date :

Pay. Date :

DMF Number : 6092

Submission : 1985-11-13

Status : Inactive

Type : II

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02

Sterling Spa

Italy

USDMF

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Not Confirmed
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NDC API

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01

Saudi International Expo
Not Confirmed
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TRILOSTANE

NDC Package Code : 60592-665

Start Marketing Date : 2023-10-13

End Marketing Date : 2024-12-31

Dosage Form (Strength) : POWDER (1g/g)

Marketing Category : BULK INGREDIENT

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02

Medisca Inc.

U.S.A
Saudi International Expo
Not Confirmed
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Medisca Inc.

U.S.A
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Saudi International Expo
Not Confirmed

TRILOSTANE

NDC Package Code : 38779-2387

Start Marketing Date : 2006-01-06

End Marketing Date : 2024-12-31

Dosage Form (Strength) : POWDER (1g/g)

Marketing Category : BULK INGREDIENT

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03

Saudi International Expo
Not Confirmed
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Saudi International Expo
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TRILOSTANE

NDC Package Code : 51927-5113

Start Marketing Date : 2020-08-31

End Marketing Date : 2025-12-31

Dosage Form (Strength) : POWDER (1kg/kg)

Marketing Category : BULK INGREDIENT FOR HUMAN P...

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04

STERLING SPA

Italy
Saudi International Expo
Not Confirmed
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STERLING SPA

Italy
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Saudi International Expo
Not Confirmed

TRILOSTANE

NDC Package Code : 64918-0725

Start Marketing Date : 2014-01-01

End Marketing Date : 2024-12-31

Dosage Form (Strength) : POWDER (1kg/kg)

Marketing Category : BULK INGREDIENT

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05

Saudi International Expo
Not Confirmed
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Saudi International Expo
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TRILOSTANE

NDC Package Code : 52128-165

Start Marketing Date : 2013-03-29

End Marketing Date : 2024-12-31

Dosage Form (Strength) : POWDER (1kg/kg)

Marketing Category : BULK INGREDIENT

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06

Saudi International Expo
Not Confirmed
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Saudi International Expo
Not Confirmed

TRILOSTANE

NDC Package Code : 52128-165

Start Marketing Date : 2013-03-29

End Marketing Date : 2025-12-31

Dosage Form (Strength) : POWDER (12kg/12kg)

Marketing Category : BULK INGREDIENT

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07

Saudi International Expo
Not Confirmed
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Saudi International Expo
Not Confirmed

TRILOSTANE

NDC Package Code : 52128-165

Start Marketing Date : 2013-03-29

End Marketing Date : 2024-12-31

Dosage Form (Strength) : POWDER (5kg/5kg)

Marketing Category : BULK INGREDIENT

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08

Saudi International Expo
Not Confirmed
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Saudi International Expo
Not Confirmed

TRILOSTANE

NDC Package Code : 52128-165

Start Marketing Date : 2013-03-29

End Marketing Date : 2025-12-31

Dosage Form (Strength) : POWDER (10kg/10kg)

Marketing Category : BULK INGREDIENT

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Saudi International Expo
Not Confirmed
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Saudi International Expo
Not Confirmed

TRILOSTANE

NDC Package Code : 52128-165

Start Marketing Date : 2013-03-29

End Marketing Date : 2024-12-31

Dosage Form (Strength) : POWDER (20kg/20kg)

Marketing Category : BULK INGREDIENT

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10

Saudi International Expo
Not Confirmed
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Saudi International Expo
Not Confirmed

TRILOSTANE

NDC Package Code : 26251-0005

Start Marketing Date : 2019-08-02

End Marketing Date : 2025-12-31

Dosage Form (Strength) : POWDER (1kg/kg)

Marketing Category : BULK INGREDIENT

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API Reference Price

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VAISHNODE"},{"dataSource":"API Import","activeIngredients":"","year":"2022","qtr":"Q3","strtotime":1661365800,"product":"VOSY-TRLT-C056-N TRILOSTANE","address":"MURASOLI MARAN TOWERS,73,MRC NAGAR","city":"CHENNAI,TAMILNADU","supplier":"DARSHENG TRADE&TECH DEVELOPMENT CO. LTD","supplierCountry":"UNITED STATES","foreign_port":"N\/A","customer":"SPICEJET LIMITED","customerCountry":"INDIA","quantity":"1.00","actualQuantity":"1000","unit":"GMS","unitRateFc":"6","totalValueFC":"6070.3","currency":"USD","unitRateINR":"483","date":"25-Aug-2022","totalValueINR":"483000","totalValueInUsd":"6070.3","indian_port":"GMR HYDERABAD AVIATION-SEZ","hs_no":"29379090","bill_no":"1003866","productDescription":"API","marketType":"REGULATED MARKET","country":"UNITED STATES","selfForZScoreResived":"Pharma Grade","supplierPort":"N\/A","supplierAddress":"N\/A","customerAddress":"MURASOLI MARAN TOWERS,73,MRC NAGAR"},{"dataSource":"API Import","activeIngredients":"","year":"2022","qtr":"Q3","strtotime":1662402600,"product":"TRILOSTANE","address":"PLOT J-137 MIDC TARAPUR,BOISAR PAL GHAR","city":"PALGHAR,MAHARASHTRA","supplier":"XIAMEN ORIGIN BIOTECH ","supplierCountry":"CHINA","foreign_port":"NA","customer":"ASHISH LIFE SCIENCE PVT LIMITED","customerCountry":"INDIA","quantity":"14.00","actualQuantity":"14","unit":"KGS","unitRateFc":"1640","totalValueFC":"23048.5","currency":"USD","unitRateINR":"131938","date":"06-Sep-2022","totalValueINR":"1847132","totalValueInUsd":"23048.5","indian_port":"BOMBAY AIR","hs_no":"29372900","bill_no":"2325563","productDescription":"API","marketType":"REGULATED MARKET","country":"CHINA","selfForZScoreResived":"Pharma Grade","supplierPort":"NA","supplierAddress":"","customerAddress":"PLOT J-137 MIDC TARAPUR,BOISAR PAL GHAR"},{"dataSource":"API Import","activeIngredients":"","year":"2022","qtr":"Q4","strtotime":1668969000,"product":"TRILOSTANE","address":"PLOT J-137 MIDC TARAPUR,BOISAR PAL GHAR","city":"PALGHAR,MAHARASHTRA","supplier":"XIAMEN ORIGIN BIOTECH ","supplierCountry":"CHINA","foreign_port":"NA","customer":"ASHISH LIFE SCIENCE PVT LIMITED","customerCountry":"INDIA","quantity":"15.00","actualQuantity":"15","unit":"KGS","unitRateFc":"1640","totalValueFC":"24897.6","currency":"USD","unitRateINR":"135464","date":"21-Nov-2022","totalValueINR":"2031960","totalValueInUsd":"24897.6","indian_port":"BOMBAY AIR","hs_no":"29372900","bill_no":"3396350","productDescription":"API","marketType":"REGULATED MARKET","country":"CHINA","selfForZScoreResived":"Pharma Grade","supplierPort":"NA","supplierAddress":"","customerAddress":"PLOT J-137 MIDC TARAPUR,BOISAR PAL GHAR"},{"dataSource":"API Import","activeIngredients":"","year":"2023","qtr":"Q1","strtotime":1676831400,"product":"TRILOSTANE","address":"PLOT J-137 MIDC TARAPUR,BOISAR PAL GHAR","city":"PALGHAR,MAHARASHTRA","supplier":"XIAMEN ORIGIN BIOTECH ","supplierCountry":"CHINA","foreign_port":"NA","customer":"ASHISH LIFE SCIENCE PVT LIMITED","customerCountry":"INDIA","quantity":"28.00","actualQuantity":"28","unit":"KGS","unitRateFc":"1470","totalValueFC":"41688.3","currency":"USD","unitRateINR":"122965.5","date":"20-Feb-2023","totalValueINR":"3443034","totalValueInUsd":"41688.3","indian_port":"BOMBAY AIR","hs_no":"29372900","bill_no":"4714686","productDescription":"API","marketType":"REGULATED MARKET","country":"CHINA","selfForZScoreResived":"Pharma Grade","supplierPort":"NA","supplierAddress":"","customerAddress":"PLOT J-137 MIDC TARAPUR,BOISAR PAL GHAR"},{"dataSource":"API Import","activeIngredients":"","year":"2023","qtr":"Q1","strtotime":1679596200,"product":"TRILOSTANE (TEST LIC. NO. TL\/AZ\/20\/002406) FOR R & D PURPOSENOT FOR SALE","address":"ZYDUS CORPORATE PARK, SCHEME NO 63, KHORAJ (GANDHINAGAR), NR. VAISHNODE","city":"AHMEDABAD","supplier":"SYMBIOTICA SPECIALITY INGREDIENTS ","supplierCountry":"MALAYSIA","foreign_port":"NA","customer":"ZYDUS LIFESCIENCES","customerCountry":"INDIA","quantity":"2.00","actualQuantity":"2","unit":"KGS","unitRateFc":"8000","totalValueFC":"16282","currency":"USD","unitRateINR":"669600","date":"24-Mar-2023","totalValueINR":"1339200","totalValueInUsd":"16282","indian_port":"BOMBAY AIR","hs_no":"29372900","bill_no":"5198271","productDescription":"API","marketType":"LESS REGULATED MARKET","country":"MALAYSIA","selfForZScoreResived":"Pharma Grade","supplierPort":"NA","supplierAddress":"","customerAddress":"ZYDUS CORPORATE PARK, SCHEME NO 63, KHORAJ (GANDHINAGAR), NR. VAISHNODE"},{"dataSource":"API Import","activeIngredients":"","year":"2024","qtr":"Q1","strtotime":1705516200,"product":"TRILOSTANE","address":"F 43 DEOLALI PLAZA, LAM ROAD,DEOLA","city":"NASIK,MAHARASHTRA","supplier":"TAIZHOU CRENE BIOTECHNOLOGY ","supplierCountry":"CHINA","foreign_port":"HANGCHOW (HANGZHOU)","customer":"REYAANSH HEALTHCARE","customerCountry":"INDIA","quantity":"6.00","actualQuantity":"6","unit":"KGS","unitRateFc":"1950","totalValueFC":"11860.2","currency":"USD","unitRateINR":"164287.5","date":"18-Jan-2024","totalValueINR":"985725","totalValueInUsd":"11860.2","indian_port":"Bombay Air","hs_no":"29372900","bill_no":"9716585","productDescription":"API","marketType":"REGULATED MARKET","country":"CHINA","selfForZScoreResived":"Pharma Grade","supplierPort":"HANGCHOW (HANGZHOU)","supplierAddress":"ECONOMIC DEVELOPED ZONE OF TAIZHOUZHEJIANG CHINA Guangzhou, , CHINASDNF CHINA","customerAddress":"F 43 DEOLALI PLAZA, LAM ROAD,DEOLA"}]
06-Feb-2021
18-Jan-2024
KGS
overview
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Average Price (USD/KGS)

Number of Transactions

Total Quantity (KGS)

Total Value (USD)

Quantity (KGS) & Unit rate (USD/KGS) over time

API Imports and Exports

Importing Country Total Quantity
(KGS)
Average Price
(USD/KGS)
Number of Transactions

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FDA Orange Book

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01

BIOENVISION

France
arrow
PODD Partnership
Not Confirmed
  • fda
  • EDQM
  • WHO-GMP

Virtual BoothSanofi is a pioneer in Diabetes Solutions, Human Vaccines, Innovative Drugs, Consumer Healthcare, and the new Genzyme.

Flag France
Digital Content Digital Content

RLD : No

TE Code :

TRILOSTANE

Brand Name : MODRASTANE

Dosage Form : CAPSULE;ORAL

Dosage Strength : 60MG

Approval Date : 1984-12-31

Application Number : 18719

RX/OTC/DISCN : DISCN

RLD : No

TE Code :

Sanofi Company Banner

02

BIOENVISION

France
arrow
PODD Partnership
Not Confirmed
  • fda
  • EDQM
  • WHO-GMP

Virtual BoothSanofi is a pioneer in Diabetes Solutions, Human Vaccines, Innovative Drugs, Consumer Healthcare, and the new Genzyme.

Flag France
Digital Content Digital Content

RLD : No

TE Code :

TRILOSTANE

Brand Name : MODRASTANE

Dosage Form : CAPSULE;ORAL

Dosage Strength : 30MG

Approval Date : 1984-12-31

Application Number : 18719

RX/OTC/DISCN : DISCN

RLD : No

TE Code :

Sanofi Company Banner
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