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Chemistry

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Also known as: 57773-63-4, Triptoreline, Arvekap, (d-trp6)-gnrh, Decapeptyl, Triptorelina
Molecular Formula
C64H82N18O13
Molecular Weight
1311.4  g/mol
InChI Key
VXKHXGOKWPXYNA-PGBVPBMZSA-N

Triptorelin Pamoate
A potent synthetic long-acting agonist of GONADOTROPIN-RELEASING HORMONE with D-tryptophan substitution at residue 6.
1 2D Structure

Triptorelin Pamoate

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(2S)-N-[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2R)-1-[[(2S)-1-[[(2S)-1-[(2S)-2-[(2-amino-2-oxoethyl)carbamoyl]pyrrolidin-1-yl]-5-(diaminomethylideneamino)-1-oxopentan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]amino]-3-(4-hydroxyphenyl)-1-oxopropan-2-yl]amino]-3-hydroxy-1-oxopropan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]amino]-3-(1H-imidazol-5-yl)-1-oxopropan-2-yl]-5-oxopyrrolidine-2-carboxamide
2.1.2 InChI
InChI=1S/C64H82N18O13/c1-34(2)23-46(56(88)75-45(13-7-21-69-64(66)67)63(95)82-22-8-14-52(82)62(94)72-31-53(65)85)76-58(90)48(25-36-28-70-42-11-5-3-9-40(36)42)78-57(89)47(24-35-15-17-39(84)18-16-35)77-61(93)51(32-83)81-59(91)49(26-37-29-71-43-12-6-4-10-41(37)43)79-60(92)50(27-38-30-68-33-73-38)80-55(87)44-19-20-54(86)74-44/h3-6,9-12,15-18,28-30,33-34,44-52,70-71,83-84H,7-8,13-14,19-27,31-32H2,1-2H3,(H2,65,85)(H,68,73)(H,72,94)(H,74,86)(H,75,88)(H,76,90)(H,77,93)(H,78,89)(H,79,92)(H,80,87)(H,81,91)(H4,66,67,69)/t44-,45-,46-,47-,48+,49-,50-,51-,52-/m0/s1
2.1.3 InChI Key
VXKHXGOKWPXYNA-PGBVPBMZSA-N
2.1.4 Canonical SMILES
CC(C)CC(C(=O)NC(CCCN=C(N)N)C(=O)N1CCCC1C(=O)NCC(=O)N)NC(=O)C(CC2=CNC3=CC=CC=C32)NC(=O)C(CC4=CC=C(C=C4)O)NC(=O)C(CO)NC(=O)C(CC5=CNC6=CC=CC=C65)NC(=O)C(CC7=CN=CN7)NC(=O)C8CCC(=O)N8
2.1.5 Isomeric SMILES
CC(C)C[C@@H](C(=O)N[C@@H](CCCN=C(N)N)C(=O)N1CCC[C@H]1C(=O)NCC(=O)N)NC(=O)[C@@H](CC2=CNC3=CC=CC=C32)NC(=O)[C@H](CC4=CC=C(C=C4)O)NC(=O)[C@H](CO)NC(=O)[C@H](CC5=CNC6=CC=CC=C65)NC(=O)[C@H](CC7=CN=CN7)NC(=O)[C@@H]8CCC(=O)N8
2.2 Synonyms
2.2.1 MeSH Synonyms

1. 6-d-tryptophan-luteinizing Hormone-releasing Factor (pig)

2. Ay 25650

3. Ay-25650

4. Ay25650

5. Cl 118532

6. Cl-118532

7. Cl118532

8. D-trp-6-lh-rh

9. Decapeptyl

10. Decapeptyl Depot

11. Decapeptyl Lp

12. Decapeptyl Trimestral

13. Embonate, Triptorelin

14. Gnrh, Trp(6)-

15. Lhrh, Trp(6)-

16. Lhrh, Tryptophyl(6)-

17. Pamoate, Triptorelin

18. Trelstar

19. Trimestral, Decapeptyl

20. Triptorelin Embonate

21. Triptorelin Pamoate

22. Wy 42462

23. Wy-42462

24. Wy42462

2.2.2 Depositor-Supplied Synonyms

1. 57773-63-4

2. Triptoreline

3. Arvekap

4. (d-trp6)-gnrh

5. Decapeptyl

6. Triptorelina

7. Triptorelinum

8. Trelstar

9. Triptodur

10. Diphereline

11. (6-d-tryptophan)luteinizing Hormone-releasing Hormone

12. Cl 118532

13. Cl-118532

14. Pglu-his-trp-ser-tyr-d-trp-leu-arg-pro-gly-nh2

15. Ay-25650

16. Luteinizing Hormone-releasing Factor (pig), 6-d-tryptophan

17. Cl 118,532

18. Chebi:63633

19. Wy 42462

20. Ay 25650

21. Pamorelin

22. Salvacyl

23. Trelstar Depot

24. 5-oxo-l-prolyl-l-histidyl-l-tryptophyl-l-seryl-l-tyrosyl-d-tryptophyl-l-leucyl-l-arginyl-l-prolylglycinamide

25. Trelstar La

26. Luteinizing Hormone-releasing Factor (swine), 6-d-tryptophan-

27. Bim 21003

28. Wy 42422

29. Tryptorelin

30. Diferelin

31. D-tryptophan-lh-rh

32. Triptoreline [inn-french]

33. Triptorelinum [inn-latin]

34. Triptorelina [inn-spanish]

35. Trellasar

36. Moapar

37. Triptorelin [usan:inn:ban]

38. Decapeptyl Sr

39. Pamorelin La

40. Unii-9081y98w2v

41. Triptorelin (swine)

42. Wy-42462

43. D-trp6-lhrh

44. Debio-8206

45. Triptorelin (usan/inn)

46. (d-trp6)-lh-rh

47. Gtpl1177

48. Schembl5079698

49. Chembl1201334

50. Dtxsid2048375

51. Schembl22289009

52. Hms2090c17

53. Ex-a3857

54. Bim-21003

55. Akos030213249

56. 9081y98w2v

57. Cs-5745

58. Db06825

59. Ncgc00167301-01

60. Ncgc00167301-02

61. As-71149

62. Bn-52014

63. Hy-12551

64. 73t634

65. C75704

66. D06247

67. [d-trp6]-lh-rh, >=97% (hplc), Powder

68. Ab01275488-01

69. A936467

70. Pglu-his-trp-ser-tyr-d-trp-leu-arg-pro-glynh2

71. Q1992452

72. (s)-1-((3s,6s,9s,12s,15r,18s,21s)-3-((1h-imidazol-5-yl)methyl)-6,15-bis((1h-indol-3-yl)methyl)-21-(3-guanidinopropyl)-12-(4-hydroxybenzyl)-9-(hydroxymethyl)-18-isobutyl-1,4,7,10,13,16,19-heptaoxo-1-((s)-5-oxopyrrolidin-2-yl)-2,5,8,11,14,17,20-heptaazadocosan-22-oyl)-n-(2-amino-2-oxoethyl)pyrrolidine-2-carboxamide

73. Glycinamide, 5-oxo-l-prolyl-l-histidyl-l-tryptophyl-l-seryl-l-tyrosyl-d-tryptophyl-l-leucyl-l-arginyl-l-prolyl-

2.3 Create Date
2008-12-10
3 Chemical and Physical Properties
Molecular Weight 1311.4 g/mol
Molecular Formula C64H82N18O13
XLogP3-0.3
Hydrogen Bond Donor Count17
Hydrogen Bond Acceptor Count15
Rotatable Bond Count33
Exact Mass1310.63087474 g/mol
Monoisotopic Mass1310.63087474 g/mol
Topological Polar Surface Area490 Ų
Heavy Atom Count95
Formal Charge0
Complexity2710
Isotope Atom Count0
Defined Atom Stereocenter Count9
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 2  
Drug NameTrelstar
PubMed HealthTriptorelin (Injection)
Drug ClassesAntineoplastic Agent, Endocrine-Metabolic Agent
Drug LabelTRELSTAR is a white to slightly yellow lyophilized cake. When reconstituted, TRELSTAR has a milky appearance. It contains a pamoate salt of triptorelin, a synthetic decapeptide agonist analog of gonadotropin releasing hormone (GnRH). The chemical...
Active IngredientTriptorelin pamoate
Dosage FormInjectable
RouteIntramuscular
Strengtheq 11.25mg base/vial; eq 3.75mg base/vial; eq 22.5mg base/vial
Market StatusPrescription
CompanyWatson Labs

2 of 2  
Drug NameTrelstar
PubMed HealthTriptorelin (Injection)
Drug ClassesAntineoplastic Agent, Endocrine-Metabolic Agent
Drug LabelTRELSTAR is a white to slightly yellow lyophilized cake. When reconstituted, TRELSTAR has a milky appearance. It contains a pamoate salt of triptorelin, a synthetic decapeptide agonist analog of gonadotropin releasing hormone (GnRH). The chemical...
Active IngredientTriptorelin pamoate
Dosage FormInjectable
RouteIntramuscular
Strengtheq 11.25mg base/vial; eq 3.75mg base/vial; eq 22.5mg base/vial
Market StatusPrescription
CompanyWatson Labs

4.2 Drug Indication

Triptorelin is indicated for the palliative treatment of advanced prostate cancer.


FDA Label


For the synchronisation of ovulation in weaned sows to enable a single fixed-time artificial insemination.


5 Pharmacology and Biochemistry
5.1 Pharmacology

The first administration of triptorelin is followed by a transient surge of follicle stimulating hormone (FSH), luteinizing hormone (LH), estradiol,and testosterone. The time, peak and decline of testosterone in the body varies depending on the dose administered. This initial surge is often responsible for worsening of prostate cancer symptoms such as urethral or bladder outlet obstruction, bone pain, spinal cord injury and hematuria in the early stages. A sustained decrease in FSH and LH, and significant reduction of testicular steroidogenesis is usually seen 2-4 weeks post-initiation of therapy. This result is a reduction of serum testosterone to levels which are typically seen in surgically castrated men. Ultimately, tissues and functions that require these hormones become inactive. The effects of triptorelin can usually be reversed once the drug is discontinued.


5.2 MeSH Pharmacological Classification

Antineoplastic Agents, Hormonal

Antineoplastic agents that are used to treat hormone-sensitive tumors. Hormone-sensitive tumors may be hormone-dependent, hormone-responsive, or both. A hormone-dependent tumor regresses on removal of the hormonal stimulus, by surgery or pharmacological block. Hormone-responsive tumors may regress when pharmacologic amounts of hormones are administered regardless of whether previous signs of hormone sensitivity were observed. The major hormone-responsive cancers include carcinomas of the breast, prostate, and endometrium; lymphomas; and certain leukemias. (From AMA Drug Evaluations Annual 1994, p2079) (See all compounds classified as Antineoplastic Agents, Hormonal.)


Luteolytic Agents

Chemical compounds that cause LUTEOLYSIS or degeneration of the CORPUS LUTEUM. (See all compounds classified as Luteolytic Agents.)


5.3 ATC Code

QH01CA97


L - Antineoplastic and immunomodulating agents

L02 - Endocrine therapy

L02A - Hormones and related agents

L02AE - Gonadotropin releasing hormone analogues

L02AE04 - Triptorelin


5.4 Absorption, Distribution and Excretion

Absorption

Following IV administration of triptorelin, triptorelin is completely absorbed.


Route of Elimination

Elimination of triptorelin involves both the kidneys and the liver.


Volume of Distribution

After a single IV dose of 0.5mg, the volume of distribution of triptorelin peptide in healthy males was 30 - 33L.


Clearance

In healthy male volunteers, total clearance of triptorelin was 211.9 mL/min.


5.5 Metabolism/Metabolites

The metabolism of triptorelin in humans is not well understood; however, metabolism likely does not involve hepatic enzymes such as cytochrome P450. Whether or not triptorelin affects, or how it affects other metabolizing enzymes is also poorly understood. Triptorelin has no identified metabolites.


5.6 Biological Half-Life

The pharmacokinetics of triptorelin follows a 3 compartment model. The half lives are estimated to be 6 minutes, 45 minutes, and 3 hours respectively.


5.7 Mechanism of Action

Triptorelin is a synthetic agonist analog of gonadotropin releasing hormone (GnRH). Animal studies comparing triptorelin to native GnRH found that triptorelin had 13 fold higher releasing activity for luteinizing hormone, and 21-fold higher releasing activity for follicle-stimulating hormone.


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Triptorelin

Brand Name : Trelstar LA 3,75 mg

Dosage Form : POI

Dosage Strength : 3.75mg

Packaging : 2X1mg

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Regulatory Info : Originator

Registration Country : South Africa

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Triptorelin

Brand Name : Trelstar LA 11,25 mg

Dosage Form : POI

Dosage Strength : 11.25mg

Packaging : 2X1mg

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Regulatory Info : Originator

Registration Country : South Africa

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Triptorelin

Brand Name : Trelstar LA 22,5 mg

Dosage Form : POI

Dosage Strength : 22.5mg

Packaging : 2X1mg

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Regulatory Info : Originator

Registration Country : South Africa

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TRIPTORELIN PAMOATE

Brand Name : TRIPTODUR KIT

Dosage Form : FOR SUSPENSION, EXTENDED RELEASE;INTRAMUSCULAR

Dosage Strength : EQ 22.5MG BASE/VIAL

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Approval Date : 2017-06-29

Application Number : 208956

Regulatory Info : RX

Registration Country : USA

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05

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Triptorelin

Brand Name : Gonapeptyl Depot

Dosage Form : Tryptoreline 3,75Mg 1 Unit Parenteral Use

Dosage Strength : 1 syringe IM SC 3.75 mg + 1 ampoule solv 1 ml

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Registration Country : Italy

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triptorelin

Brand Name : Decapeptyl

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Packaging : 7

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Registration Country : Australia

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Ipsen

France
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Ipsen

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triptorelin

Brand Name : Diphereline

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Packaging : 1

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Registration Country : Australia

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TRIPTORELIN (TRIPTORELIN PAMOATE)

Brand Name : TRELSTAR

Dosage Form : POWDER FOR SUSPENSION, SUSTAINED-RELEASE

Dosage Strength : 11.25MG/VIAL

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Approval Date :

Application Number : 2243856

Regulatory Info : Prescription

Registration Country : Canada

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Triptorelin

Brand Name :

Dosage Form : Injection

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Packaging : Three Months Depot

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Registration Country : Iran

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10

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triptorelinembonat

Brand Name : Pamorelin

Dosage Form : POWDER AND SOLVENT FOR SOLUTION FOR INJECTION

Dosage Strength : 22.5 MG

Packaging :

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Regulatory Info :

Registration Country : Sweden

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Europe

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01

Medlab Asia & Asia Health
Not Confirmed
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Medlab Asia & Asia Health
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Triptorelinum

Brand Name : Pamorelin LA

Dosage Form : Trockensub

Dosage Strength : 11.25mg

Packaging :

Approval Date :

Application Number :

Regulatory Info :

Registration Country : Switzerland

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02

Medlab Asia & Asia Health
Not Confirmed
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Medlab Asia & Asia Health
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Triptorelinum

Brand Name : Pamorelin LA

Dosage Form : Trockensub

Dosage Strength : 3.75mg

Packaging :

Approval Date :

Application Number :

Regulatory Info :

Registration Country : Switzerland

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03

Medlab Asia & Asia Health
Not Confirmed
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Medlab Asia & Asia Health
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Triptorelinum

Brand Name : Pamorelin LA

Dosage Form : Trockensub

Dosage Strength : 22.5mg

Packaging :

Approval Date :

Application Number :

Regulatory Info :

Registration Country : Switzerland

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04

Medlab Asia & Asia Health
Not Confirmed
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Medlab Asia & Asia Health
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Triptorelin

Brand Name : Gonapeptyl

Dosage Form : Injection fluid, resolution

Dosage Strength : 0.1 mg/ml

Packaging : Finish filled syringe

Approval Date :

Application Number :

Regulatory Info :

Registration Country : Norway

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05

Ferring AG

Switzerland
Medlab Asia & Asia Health
Not Confirmed
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Ferring AG

Switzerland
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Medlab Asia & Asia Health
Not Confirmed

Triptorelini acetas hydricus

Brand Name : Decapeptyl

Dosage Form : Inj L?s

Dosage Strength : 0.1mg/ml

Packaging :

Approval Date :

Application Number :

Regulatory Info :

Registration Country : Switzerland

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06

IPSEN SpA

France
Medlab Asia & Asia Health
Not Confirmed
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IPSEN SpA

France
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Medlab Asia & Asia Health
Not Confirmed

Triptorelin

Brand Name : Decapeptyl

Dosage Form : Tryptoreline 3,75Mg 1 Unit Parenteral Use

Dosage Strength : 1 vial IM 3.75 mg + 1 ampoule solv 2 ml + 1 syringe

Packaging :

Approval Date :

Application Number :

Regulatory Info :

Registration Country : Italy

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07

IPSEN SpA

France
Medlab Asia & Asia Health
Not Confirmed
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IPSEN SpA

France
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Medlab Asia & Asia Health
Not Confirmed

Triptorelin

Brand Name : Decapeptyl

Dosage Form : Tryptoreline 11,25Mg 1 Unit Parenteral Use

Dosage Strength : 1 vial IM 11.25 mg + 1 ampoule solv 2 ml + 1 syringe

Packaging :

Approval Date :

Application Number :

Regulatory Info :

Registration Country : Italy

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08

IPSEN SpA

France
Medlab Asia & Asia Health
Not Confirmed
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IPSEN SpA

France
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Medlab Asia & Asia Health
Not Confirmed

Triptorelin

Brand Name : Decapeptyl

Dosage Form :

Dosage Strength : 7 Vials 0.1 Mg + 7 Vials Solv  

Packaging :

Approval Date :

Application Number :

Regulatory Info :

Registration Country : Italy

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09

Laboratoires Sodia

Country
Medlab Asia & Asia Health
Not Confirmed
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Laboratoires Sodia

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Medlab Asia & Asia Health
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triptorelinembonat

Brand Name : Moapar

Dosage Form : PULVER OCH VÄTSKA TILL INJEKTIONSVÄTSKA

Dosage Strength : 11,25 MG

Packaging :

Approval Date :

Application Number :

Regulatory Info :

Registration Country : Sweden

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10

Institute Produits Synthèse

Country
Medlab Asia & Asia Health
Not Confirmed
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Institute Produits Synthèse

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Medlab Asia & Asia Health
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triptorelinembonat

Brand Name : Pamorelin

Dosage Form : POWDER AND SOLVENT FOR SOLUTION FOR INJECTION

Dosage Strength : 11.25 MG

Packaging :

Approval Date :

Application Number :

Regulatory Info :

Registration Country : Sweden

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DRUG PRODUCT COMPOSITIONS

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DOSAGE - INJECTABLE;INTRAMUSCULAR - EQ 3.75MG...DOSAGE - INJECTABLE;INTRAMUSCULAR - EQ 3.75MG BASE/VIAL

USFDA APPLICATION NUMBER - 20715

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DOSAGE - INJECTABLE;INTRAMUSCULAR - EQ 11.25M...DOSAGE - INJECTABLE;INTRAMUSCULAR - EQ 11.25MG BASE/VIAL

USFDA APPLICATION NUMBER - 21288

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DOSAGE - INJECTABLE;INTRAMUSCULAR - EQ 22.5MG...DOSAGE - INJECTABLE;INTRAMUSCULAR - EQ 22.5MG BASE/VIAL

USFDA APPLICATION NUMBER - 22437

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Finished Drug Prices

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01

Brand Name : Decapeptyl

France
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Medlab Asia & Asia Health
Not Confirmed

Brand Name : Decapeptyl

France
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Medlab Asia & Asia Health
Not Confirmed

Triptorelin Pamoate

Dosage Form :

Dosage Strength : 7 Vials 0.1 Mg + 7 Vials Solv  

Price Per Pack (Euro) : 44.78

Published in :

Country : Italy

RX/OTC/DISCN : Class C

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02

Brand Name : Decapeptyl

Switzerland
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Medlab Asia & Asia Health
Not Confirmed

Brand Name : Decapeptyl

Switzerland
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Medlab Asia & Asia Health
Not Confirmed

Triptorelin Pamoate

Dosage Form : Inj L?s

Dosage Strength : 0.1mg/ml

Price Per Pack (Euro) : 45.38

Published in :

Country : Switzerland

RX/OTC/DISCN : Class A

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03

Brand Name : Gonapeptyl

Switzerland
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Medlab Asia & Asia Health
Not Confirmed

Brand Name : Gonapeptyl

Switzerland
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Medlab Asia & Asia Health
Not Confirmed

Triptorelin Pamoate

Dosage Form : Injection fluid, resolution

Dosage Strength : 0.1 mg/ml

Price Per Pack (Euro) : 47.531

Published in :

Country : Norway

RX/OTC/DISCN :

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04

Brand Name : Pamorelin LA

Switzerland
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Medlab Asia & Asia Health
Not Confirmed

Brand Name : Pamorelin LA

Switzerland
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Medlab Asia & Asia Health
Not Confirmed

Triptorelin Pamoate

Dosage Form : Trockensub

Dosage Strength : 11.25mg

Price Per Pack (Euro) : 320.02

Published in :

Country : Switzerland

RX/OTC/DISCN : Class A

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05

Brand Name : Pamorelin LA

Switzerland
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Medlab Asia & Asia Health
Not Confirmed

Brand Name : Pamorelin LA

Switzerland
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Medlab Asia & Asia Health
Not Confirmed

Triptorelin Pamoate

Dosage Form : Trockensub

Dosage Strength : 3.75mg

Price Per Pack (Euro) : 110.49

Published in :

Country : Switzerland

RX/OTC/DISCN : Class A

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06

Brand Name : Pamorelin LA

Switzerland
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Medlab Asia & Asia Health
Not Confirmed

Brand Name : Pamorelin LA

Switzerland
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Medlab Asia & Asia Health
Not Confirmed

Triptorelin Pamoate

Dosage Form : Trockensub

Dosage Strength : 22.5mg

Price Per Pack (Euro) : 589.5

Published in :

Country : Switzerland

RX/OTC/DISCN : Class A

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07

Brand Name : Salvacyl

Switzerland
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Medlab Asia & Asia Health
Not Confirmed

Brand Name : Salvacyl

Switzerland
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Medlab Asia & Asia Health
Not Confirmed

Triptorelin Pamoate

Dosage Form : Trockensub

Dosage Strength : 11.25mg

Price Per Pack (Euro) : 292.07

Published in :

Country : Switzerland

RX/OTC/DISCN : Class B

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08

Brand Name : Pamorelin

Country
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Medlab Asia & Asia Health
Not Confirmed

Brand Name : Pamorelin

Country
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Medlab Asia & Asia Health
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Triptorelin Pamoate

Dosage Form : Powder and liquid to depot injec...

Dosage Strength : 11.25 mg

Price Per Pack (Euro) : 311.81

Published in :

Country : Norway

RX/OTC/DISCN :

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09

Brand Name : Pamorelin

Country
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Medlab Asia & Asia Health
Not Confirmed

Brand Name : Pamorelin

Country
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Medlab Asia & Asia Health
Not Confirmed

Triptorelin Pamoate

Dosage Form : Powder and liquid to depot injec...

Dosage Strength : 22.5 mg

Price Per Pack (Euro) : 637.42

Published in :

Country : Norway

RX/OTC/DISCN :

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10

Brand Name : Pamorelin

Country
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Medlab Asia & Asia Health
Not Confirmed

Brand Name : Pamorelin

Country
arrow
Medlab Asia & Asia Health
Not Confirmed

Triptorelin Pamoate

Dosage Form : Powder and liquid to depot injec...

Dosage Strength : 3.75 mg

Price Per Pack (Euro) : 123.49

Published in :

Country : Norway

RX/OTC/DISCN :

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