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Chemistry

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Also known as: Dermatop, 73771-04-7, Hoe 777, Hoe-777, Dermatop e emollient, S-770777
Molecular Formula
C27H36O8
Molecular Weight
488.6  g/mol
InChI Key
FNPXMHRZILFCKX-KAJVQRHHSA-N
FDA UNII
V901LV1K7D

Prednicarbate
Prednicarbate is a synthetic non-halogenated double-ester derivative of the corticosteroid prednisolone with anti-inflammatory, antipruritic and vasoconstrictive properties. Following skin permeation, prednicarbate enters cells and binds to and activates specific nuclear receptors, resulting in an altered gene expression and inhibition of pro-inflammatory cytokine production by increasing the expression of lipocortins. These block phospholipase A-dependent release of arachidonic acid thereby inhibiting prostaglandin synthesis. This agent also decreases the number of circulating lymphocytes by suppression of the production of vasodilators such as prostacyclin and nitric oxide.
Prednicarbate is a Corticosteroid. The mechanism of action of prednicarbate is as a Corticosteroid Hormone Receptor Agonist.
1 2D Structure

Prednicarbate

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
[2-[(8S,9S,10R,11S,13S,14S,17R)-17-ethoxycarbonyloxy-11-hydroxy-10,13-dimethyl-3-oxo-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-yl]-2-oxoethyl] propanoate
2.1.2 InChI
InChI=1S/C27H36O8/c1-5-22(31)34-15-21(30)27(35-24(32)33-6-2)12-10-19-18-8-7-16-13-17(28)9-11-25(16,3)23(18)20(29)14-26(19,27)4/h9,11,13,18-20,23,29H,5-8,10,12,14-15H2,1-4H3/t18-,19-,20-,23+,25-,26-,27-/m0/s1
2.1.3 InChI Key
FNPXMHRZILFCKX-KAJVQRHHSA-N
2.1.4 Canonical SMILES
CCC(=O)OCC(=O)C1(CCC2C1(CC(C3C2CCC4=CC(=O)C=CC34C)O)C)OC(=O)OCC
2.1.5 Isomeric SMILES
CCC(=O)OCC(=O)[C@]1(CC[C@@H]2[C@@]1(C[C@@H]([C@H]3[C@H]2CCC4=CC(=O)C=C[C@]34C)O)C)OC(=O)OCC
2.2 Other Identifiers
2.2.1 UNII
V901LV1K7D
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Batmen

2. Dermatop

3. Hoe 777

4. Hoe-777

5. Peitel

6. Prednisolone-17-ethylcarbonate-21-propionate

2.3.2 Depositor-Supplied Synonyms

1. Dermatop

2. 73771-04-7

3. Hoe 777

4. Hoe-777

5. Dermatop E Emollient

6. S-770777

7. Mls002154121

8. V901lv1k7d

9. Las189961

10. S 77 0777

11. S-77 0777

12. Las-189961

13. Nsc-760042

14. Peitel

15. Las-41003 Component Prednicarbate

16. Unii-v901lv1k7d

17. S-77-0777

18. Prednicarbato

19. Prednicarbatum

20. [2-[(8s,9s,10r,11s,13s,14s,17r)-17-ethoxycarbonyloxy-11-hydroxy-10,13-dimethyl-3-oxo-7,8,9,11,12,14,15,16-octahydro-6h-cyclopenta[a]phenanthren-17-yl]-2-oxoethyl] Propanoate

21. Dermatop (tn)

22. Prednicarbate (usp/inn)

23. Prednicarbatum [inn-latin]

24. Prednicarbat

25. Prednicarbato [inn-spanish]

26. Ncgc00016926-01

27. Einecs 277-590-3

28. Prednicarbate [usan:usp:inn:ban]

29. Cas-73771-04-7

30. Prestwick0_001044

31. Prestwick1_001044

32. Prestwick2_001044

33. Prestwick3_001044

34. Prednicarbate [mi]

35. Prednicarbate [inn]

36. Schembl3941

37. Dsstox_cid_25502

38. Dsstox_rid_80919

39. Prednicarbate [usan]

40. Dsstox_gsid_45502

41. Bspbio_000968

42. Prednicarbate [vandf]

43. Prednicarbate [mart.]

44. S 770777

45. Spbio_002904

46. Prednicarbate [usp-rs]

47. Prednicarbate [who-dd]

48. Bpbio1_001066

49. Gtpl7605

50. Chembl1200386

51. Dtxsid9045502

52. Chebi:135791

53. Hms1571a10

54. Hms2098a10

55. Hms2230o11

56. Hms3715a10

57. Prednicarbate [orange Book]

58. Hy-b1365

59. Zinc3938652

60. Prednicarbate [ep Monograph]

61. Tox21_110687

62. Prednicarbate [usp Monograph]

63. Akos025402043

64. Prednicarbate For System Suitability A

65. Ac-3521

66. Ccg-221044

67. Db01130

68. Nsc 760042

69. 11beta,17,21-trihydroxypregna-1,4-diene-3,20-dione 17-(ethyl Carbonate) 21-propionate

70. Ncgc00179357-01

71. Ncgc00179357-05

72. Pregna-1,4-diene-3,20-dione, 17-((ethoxycarbonyl)oxy)-11-hydroxy-21-(1-oxopropoxy)-, (11beta)-

73. Smr001233428

74. Ab00514017

75. Cs-0013106

76. D05601

77. 771p047

78. Sr-01000841201

79. Q-101379

80. Q4376623

81. Sr-01000841201-2

82. Brd-k46137903-001-03-3

83. 11.beta.,17,21-trihydroxypregna-1,4-diene-3,20-dione 17-(ethyl Carbonate) 21-propionate

84. Pregna-1,4-diene-3,20-dione, 17-((ethoxycarbonyl)oxy)-11-hydroxy-21-(1-oxopropoxy)-, (11.beta.)-

2.4 Create Date
2006-06-05
3 Chemical and Physical Properties
Molecular Weight 488.6 g/mol
Molecular Formula C27H36O8
XLogP34.2
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count8
Rotatable Bond Count9
Exact Mass488.24101810 g/mol
Monoisotopic Mass488.24101810 g/mol
Topological Polar Surface Area116 Ų
Heavy Atom Count35
Formal Charge0
Complexity982
Isotope Atom Count0
Defined Atom Stereocenter Count7
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Information
1 of 6  
Drug NameDermatop
PubMed HealthPrednicarbate (Topical application route)
Drug ClassesAdrenal Glucocorticoid, Corticosteroid, Intermediate
Drug LabelDERMATOP Ointment (prednicarbate ointment) 0.1% contains the non-halogenated prednisolone derivative prednicarbate. The topical corticosteroids constitute a class of primarily synthetic steroids used topically as anti-inflammatory and anti-pruritic...
Active IngredientPrednicarbate
Dosage FormOintment
RouteTopical
Strength0.1%
Market StatusPrescription
CompanyValeant Bermuda

2 of 6  
Drug NameDermatop e emollient
PubMed HealthPrednicarbate (Topical application route)
Drug ClassesAdrenal Glucocorticoid, Corticosteroid, Intermediate
Drug LabelDERMATOP Ointment (prednicarbate ointment) 0.1% contains the non-halogenated prednisolone derivative prednicarbate. The topical corticosteroids constitute a class of primarily synthetic steroids used topically as anti-inflammatory and anti-pruritic...
Active IngredientPrednicarbate
Dosage FormCream
RouteTopical
Strength0.1%
Market StatusPrescription
CompanyValeant Bermuda

3 of 6  
Drug NamePrednicarbate
Active IngredientPrednicarbate
Dosage FormOintment; Cream
RouteTopical
Strength0.1%
Market StatusPrescription
CompanyFougera Pharms

4 of 6  
Drug NameDermatop
PubMed HealthPrednicarbate (Topical application route)
Drug ClassesAdrenal Glucocorticoid, Corticosteroid, Intermediate
Drug LabelDERMATOP Ointment (prednicarbate ointment) 0.1% contains the non-halogenated prednisolone derivative prednicarbate. The topical corticosteroids constitute a class of primarily synthetic steroids used topically as anti-inflammatory and anti-pruritic...
Active IngredientPrednicarbate
Dosage FormOintment
RouteTopical
Strength0.1%
Market StatusPrescription
CompanyValeant Bermuda

5 of 6  
Drug NameDermatop e emollient
PubMed HealthPrednicarbate (Topical application route)
Drug ClassesAdrenal Glucocorticoid, Corticosteroid, Intermediate
Drug LabelDERMATOP Ointment (prednicarbate ointment) 0.1% contains the non-halogenated prednisolone derivative prednicarbate. The topical corticosteroids constitute a class of primarily synthetic steroids used topically as anti-inflammatory and anti-pruritic...
Active IngredientPrednicarbate
Dosage FormCream
RouteTopical
Strength0.1%
Market StatusPrescription
CompanyValeant Bermuda

6 of 6  
Drug NamePrednicarbate
Active IngredientPrednicarbate
Dosage FormOintment; Cream
RouteTopical
Strength0.1%
Market StatusPrescription
CompanyFougera Pharms

4.2 Drug Indication

For the relief of the inflammatory and pruritic manifestations of corticosteroid-responsive dermatoses.


FDA Label


5 Pharmacology and Biochemistry
5.1 Pharmacology

Corticosteroids diffuse across cell membranes and complex with specific cytoplasmic receptors. These complexes then enter the cell nucleus, bind to DNA (chromatin), and stimulate transcription of messenger RNA (mRNA) and subsequent protein synthesis of various inhibitory enzymes responsible for the anti-inflammatory effects of topical corticosteroids. These anti-inflammatory effects include inhibition of early processes such as edema, fibrin deposition, capillary dilatation, movement of phagocytes into the area, and phagocytic activities. Later processes, such as capillary production, collagen deposition, and keloid formation also are inhibited by corticosteroids.


5.2 MeSH Pharmacological Classification

Anti-Inflammatory Agents

Substances that reduce or suppress INFLAMMATION. (See all compounds classified as Anti-Inflammatory Agents.)


Glucocorticoids

A group of CORTICOSTEROIDS that affect carbohydrate metabolism (GLUCONEOGENESIS, liver glycogen deposition, elevation of BLOOD SUGAR), inhibit ADRENOCORTICOTROPIC HORMONE secretion, and possess pronounced anti-inflammatory activity. They also play a role in fat and protein metabolism, maintenance of arterial blood pressure, alteration of the connective tissue response to injury, reduction in the number of circulating lymphocytes, and functioning of the central nervous system. (See all compounds classified as Glucocorticoids.)


5.3 FDA Pharmacological Classification
5.3.1 Active Moiety
PREDNICARBATE
5.3.2 FDA UNII
V901LV1K7D
5.3.3 Pharmacological Classes
Corticosteroid [EPC]; Corticosteroid Hormone Receptor Agonists [MoA]
5.4 ATC Code

D - Dermatologicals

D07 - Corticosteroids, dermatological preparations

D07A - Corticosteroids, plain

D07AC - Corticosteroids, potent (group iii)

D07AC18 - Prednicarbate


5.5 Absorption, Distribution and Excretion

Absorption

Absorbed systemically across the stratum corneum.


5.6 Metabolism/Metabolites

Primarily in skin


5.7 Mechanism of Action

In common with other topical corticosteroids, prednicarbate has anti-inflammatory, antipruritic, and vasoconstrictive properties. In general, the mechanism of the anti-inflammatory activity of topical steroids is unclear. However, corticosteroids are thought to act by the induction of phospholipase A2 inhibitory proteins, collectively called lipocortins. It is postulated that these proteins control the biosynthesis of potent mediators of inflammation such as prostaglandins and leukotrienes by inhibiting the release of their common precursor arachidonic acid. Arachidonic acid is released from membrane phospholipids by phospholipase A2.


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GDUFA

DMF Review : N/A

Rev. Date :

Pay. Date :

DMF Number : 17031

Submission : 2003-12-19

Status : Active

Type : II

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CEP 2011-144 - Rev 03
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2024-08-19
1467
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Certificate Number : CEP 2011-144 - Rev 03

Status : Valid

Issue Date : 2024-08-19

Type : Chemical

Substance Number : 1467

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R1-CEP 2009-014 - Rev 01
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Certificate Number : R1-CEP 2009-014 - Rev 01

Status : Valid

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Type : Chemical

Substance Number : 1467

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Prednicarbate

Registrant Name : Sungjin Exim Co., Ltd.

Registration Date : 2020-06-05

Registration Number : 20200605-211-J-650

Manufacturer Name : NEWCHEM SpA@IMS . SrI@Henan ...

Manufacturer Address : Via Roveggia, 47-37136 Verona(VR) Italy@Via Venezia Giulia 23-20157 Milano(MI) Italy@...

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PREDNICARBATE

NDC Package Code : 65089-0032

Start Marketing Date : 1991-09-23

End Marketing Date : 2024-12-31

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

Marketing Category : BULK INGREDIENT FOR HUMAN P...

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PREDNICARBATE

NDC Package Code : 24002-0006

Start Marketing Date : 2009-08-10

End Marketing Date : 2024-12-31

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

Marketing Category : BULK INGREDIENT

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NDC Package Code : 63592-2140

Start Marketing Date : 2018-10-19

End Marketing Date : 2024-12-31

Dosage Form (Strength) : POWDER (100kg/100kg)

Marketing Category : BULK INGREDIENT

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NDC Package Code : 52128-168

Start Marketing Date : 2013-05-06

End Marketing Date : 2024-12-31

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

Marketing Category : BULK INGREDIENT

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About the Company : Axplora, created from the merger of Farmabios, Novasep & PharmaZell, is a leading API manufacturing partner to the world’s leading pharma & biotech companies, delivering top-qual...

Axplora, created from the merger of Farmabios, Novasep & PharmaZell, is a leading API manufacturing partner to the world’s leading pharma & biotech companies, delivering top-quality APIs on time & at scale, to the highest industry standards. It is dedicated to helping pharma companies make critical medicines safely to benefit patients. Leveraging our combined expertise & manufacturing capabilities across 9 industrial sites in the EU & India & an R&D facility in the USA, it offers CDMO services for small molecule APIs & biopharmaceuticals to innovators as well as APIs that address lifestyle-induced respiratory, inflammatory & liver diseases.
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About the Company : EUROAPI is the market leader in small molecule APIs with projected sales of about €1 billion in 2022. With around 200 APIs, it has one of the largest portfolios in the market. Th...

EUROAPI is the market leader in small molecule APIs with projected sales of about €1 billion in 2022. With around 200 APIs, it has one of the largest portfolios in the market. Thanks to its excellent R&D skills and six manufacturing facilities across Europe, EUROAPI guarantees API manufacturing of the highest quality to its clients in over 80 countries. Its strong innovation and R&D skills helps it to speed the development of more complex molecule segments through CDMO operations. It also offers experience in supply, regulation and quality. EUROAPI employs 3,350 people and is listed on Euronext.
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About the Company : Curia is a global contract research, development and manufacturing organization (CDMO), offering products and services across the drug development spectrum to help our partners tur...

Curia is a global contract research, development and manufacturing organization (CDMO), offering products and services across the drug development spectrum to help our partners turn their ideas into real-world impact. We partner closely with pharmaceutical and biotechnology companies to boost business performance and improve patients’ lives. From early discovery and development through manufacturing and commercialization, our suite of custom solutions allows us to tailor every engagement to your precise needs, whether that’s an independent project or an opportunity that cuts across the drug continuum.
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About the Company : Guangzhou Topwork Chemical Co., Ltd. Specializes in manufacturing corticosteroid and relative intermediates. We provide high quality products and excellent service to our clients a...

Guangzhou Topwork Chemical Co., Ltd. Specializes in manufacturing corticosteroid and relative intermediates. We provide high quality products and excellent service to our clients and have gained a high business reputation in the world market. Topwork gathers a group of energetic, hardworking and much experienced experts. They dedicate their entire efforts to research and development of new products. To guarantee the quality of our products, we have established an international standard quality control system. All of our products conform the latest standard of USP, EP, BP and CP.
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About the Company : NEWCHEM is an independent Italian manufacturer of Active Pharmaceutical Ingredients (APIs) - Steroids, Progestogens, Prostafglandins. NEWCHEM is active on the worldwide Pharmaceut...

NEWCHEM is an independent Italian manufacturer of Active Pharmaceutical Ingredients (APIs) - Steroids, Progestogens, Prostafglandins. NEWCHEM is active on the worldwide Pharmaceutical Manufacturing market. Quality and reliability are guaranteed by the proven experience of EFFECHEM. NEWCHEM recruits only highly specialized personnel to work in compliance with the strictest regulations.The company is constantly updating its procedures to meet the most advanced quality and safety requirements.
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About the Company : Symbiotica is a Manufacturer of APIs from Malaysia with a cGMP Steroidal facility at Kulim, a Pioneer status from Malaysian Industrial Development Authority and P.I.C/S & W.H.O GMP...

Symbiotica is a Manufacturer of APIs from Malaysia with a cGMP Steroidal facility at Kulim, a Pioneer status from Malaysian Industrial Development Authority and P.I.C/S & W.H.O GMP certified as well as ISO 9001:2000 certified. USDMFs /CTDs have been filed on several products. We have CEPs for Dexamethasone sodium phosphate, Betamethasone valerate, Betamethasone Dipropionate, Clobetasol propionate, Mometasone furoate & Tibolone. Global Market segments include Regulated, Semi- Regulated & Non-regulated Markets. Other Key products are Betamethasones, Clobetasol, Deflazacort, Exemestane, Fluticasone, Fluocinonide.
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Regulatory Info :

Registration Country : Italy

Prednicarbate

Brand Name : Atop

Dosage Form : Prednicarbate 0.25% 30G Ointment Dermatological Use

Dosage Strength : cream derm 30 g 0.25%

Packaging :

Approval Date :

Application Number :

Regulatory Info :

Registration Country : Italy

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Prednicarbatum

Brand Name : Prednicutan

Dosage Form : Ointment

Dosage Strength : 2.5mg/g

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Regulatory Info :

Registration Country : Switzerland

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Prednicarbatum

Brand Name : Prednicutan Crinale

Dosage Form : Solution

Dosage Strength : 2.5mg/g

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Registration Country : Switzerland

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Prednicarbate

Brand Name : Batmen 0.25% 30G Cream

Dosage Form : Cream

Dosage Strength : 2.5 Mg/Cream

Packaging :

Approval Date :

Application Number :

Regulatory Info :

Registration Country : Spain

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Prednicarbate

Brand Name : Batmen 0.25% 30G Ointment

Dosage Form : Ointment

Dosage Strength : 2.5 Mg/Ointment

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Registration Country : Spain

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Prednicarbate

Brand Name : Peitel Ointment 1 Tube Of 30G

Dosage Form : Ointment

Dosage Strength : 2.5 Mg/Ointment

Packaging :

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Regulatory Info :

Registration Country : Spain

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Prednicarbate

Brand Name : Batmen 0.25% 60G Cream

Dosage Form : Cream

Dosage Strength : 2.5 Mg/Cream

Packaging :

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Regulatory Info :

Registration Country : Spain

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Brand Name : Peitel Ointment 1 Tube Of 60G

Dosage Form : Ointment

Dosage Strength : 2.5 Mg/Ointment

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Regulatory Info :

Registration Country : Spain

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Brand Name : Batmen 0.25% 60G Ointment

Dosage Form : Ointment

Dosage Strength : 2.5 Mg/Ointment

Packaging :

Approval Date :

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Registration Country : Spain

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Prednicarbate

Brand Name : 1 Peitel Solution 60Ml

Dosage Form : Solution

Dosage Strength : 2.5 Mg/Solution

Packaging :

Approval Date :

Application Number :

Regulatory Info :

Registration Country : Spain

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DRUG PRODUCT COMPOSITIONS

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DOSAGE - OINTMENT;TOPICAL - 0.1% **Federal Re...DOSAGE - OINTMENT;TOPICAL - 0.1% **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

USFDA APPLICATION NUMBER - 19568

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DOSAGE - CREAM;TOPICAL - 0.1% **Federal Regis...DOSAGE - CREAM;TOPICAL - 0.1% **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

USFDA APPLICATION NUMBER - 20279

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Excipients by Applications

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Topical

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01

DKSH

Switzerland
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CPHI Middle east
Not Confirmed
  • fda
  • EDQM
  • WHO-GMP

Virtual BoothDKSH is your trusted partner for companies looking to grow their business in Asia & beyond.

Grade : Topical, Parenteral

Category : Solubilizers, Topical

02

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CPHI Middle east
Not Confirmed
  • fda
  • EDQM
  • WHO-GMP

Virtual BoothNanjing Well is focused on R&D, production & sales of Pharmaceutical Excipients & Synthetic Lubricating base oils.

Grade : Topical

Category : Emulsifying Agents, Surfactant & Foaming Agents, Topical

03

arrow
CPHI Middle east
Not Confirmed
  • fda
  • EDQM
  • WHO-GMP

Virtual BoothNanjing Well is focused on R&D, production & sales of Pharmaceutical Excipients & Synthetic Lubricating base oils.

04

arrow
CPHI Middle east
Not Confirmed
  • fda
  • EDQM
  • WHO-GMP

Virtual BoothNanjing Well is focused on R&D, production & sales of Pharmaceutical Excipients & Synthetic Lubricating base oils.

Grade : Topical

Category : Topical

Brand Name : Octyldodecanol

Excipient Details : Octyldodecanol is used as a solvent in topical dosage forms.

Pharmacopoeia Ref : USP/EP

Technical Specs : NA

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07

BASF

Germany
CPHI Middle east
Not Confirmed
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Lubricants & Glidants

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Fillers, Diluents & Binders

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Emulsifying Agents

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Thickeners and Stabilizers

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Solubilizers

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API Stability Enhancers

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Film Formers & Plasticizers

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Direct Compression

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Surfactant & Foaming Agents

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Controlled & Modified Release

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Parenteral

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Co-Processed Excipients

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