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Cytisine

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Chemistry

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Also known as: 485-35-8, Sophorine, Baptitoxine, Cytiton, Baptitoxin, Cytisinicline

Molecular Formula

C₁₁H₁₄N₂O

Molecular Weight

190.24 g/mol

InChI Key

ANJTVLIZGCUXLD-DTWKUNHWSA-N

FDA UNII

53S5U404NU

cytisine is a natural product found in Viscum cruciatum, Thermopsis chinensis, and other organisms with data available.

1 2D Structure

Cytisine

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(1R,9S)-7,11-diazatricyclo[7.3.1.02,7]trideca-2,4-dien-6-one

2.1.2 InChI

InChI=1S/C11H14N2O/c14-11-3-1-2-10-9-4-8(5-12-6-9)7-13(10)11/h1-3,8-9,12H,4-7H2/t8-,9+/m0/s1

2.1.3 InChI Key

ANJTVLIZGCUXLD-DTWKUNHWSA-N

2.1.4 Canonical SMILES

C1C2CNCC1C3=CC=CC(=O)N3C2

2.1.5 Isomeric SMILES

C1[C@H]2CNC[C@@H]1C3=CC=CC(=O)N3C2

2.2 Other Identifiers

2.2.1 UNII

53S5U404NU

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 3-hydroxy-11-norcytisine

2. Citizine

3. Cystisin

4. Cytisine Dihydrochloride, Trihydrate

5. Cytisine Hydrochloride

6. Cytisine Hydrochloride, Hydrate

7. Cytisine Tetrahydrochloride, Trihydrate

8. Cytiton

9. Tabex

10. Tsitizin

2.3.2 Depositor-Supplied Synonyms

1. 485-35-8

2. Sophorine

3. Baptitoxine

4. Cytiton

5. Baptitoxin

6. Cytisinicline

7. Laburnin

8. Tabex

9. Ulexine

10. Ulexin

11. (-)-cytisine

12. Citizin

13. Cytitone

14. Tsitizin

15. Cystisine

16. Cytizin

17. Tabax

18. Baphitoxine

19. (1r,5s)-3,4,5,6-tetrahydro-1h-1,5-methanopyrido[1,2-a][1,5]diazocin-8(2h)-one

20. (1r,5s)-1,2,3,4,5,6-hexahydro-8h-1,5-methanopyrido[1,2-a][1,5]diazocin-8-one

21. 6039 Sopharma

22. Cytisin

23. Cytisine (-)

24. Cytisinicline [usan]

25. Nsc-407282

26. Chebi:4055

27. Chembl497939

28. 53s5u404nu

29. (1r,9s)-7,11-diazatricyclo[7.3.1.0^{2,7}]trideca-2,4-dien-6-one

30. (1r,9s)-7,11-diazatricyclo[7.3.1.02,7]trideca-2,4-dien-6-one

31. Nsc 407282

32. Brn 0083882

33. 1,5-methano-8h-pyrido(1,2-a)(1,5)diazocin-8-one, 1,2,3,4,5,6-hexahydro-, (1r,5s)-

34. 1,5-methano-8h-pyrido[1,2-a][1,5]diazocin-8-one, 1,2,3,4,5,6-hexahydro-, (1r,5s)-

35. Smr001233264

36. Hsdb 3560

37. Mls003171607

38. Einecs 207-616-0

39. Unii-53s5u404nu

40. Mfcd00136048

41. Nsc407282

42. 1,2,3,4,5,6-hexahydro-1,5-methano-8h-pyrido(1,2-a)(1,5)diazocin-8-one

43. Cytisine- Bio-x

44. C5e

45. Prestwick_140

46. Cytisine ((+)-)

47. Tocris-1390

48. Cytisine [hsdb]

49. Cytisine [mi]

50. Prestwick3_000624

51. Cytisine [mart.]

52. Cytisinicline [inn]

53. (1r,5s)-1,2,3,4,5,6-hexahydro-1,5-methano-8h-pyrido[1,2-a][1,5]diazocin-8-one

54. Bspbio_000588

55. Cytisine, >=99%, Powder

56. 5-24-02-00535 (beilstein Handbook Reference)

57. Mls002153916

58. Mls002222174

59. Schembl161398

60. Cytisinicline [who-dd]

61. Bpbio1_000648

62. Gtpl5347

63. (1r,9r)-7,11-diazatricyclo[7.3.1.0~2,7~]trideca-2,4-dien-6-one

64. (1s,9r)-7,11-diazatricyclo[7.3.1.0~2,7~]trideca-2,4-dien-6-one

65. 1,2,3,4,5,6-hexahydro-1,5-methano-pyrido[1,2-a][1,5]diazocin-8-one

66. Dtxsid00883395

67. 1,2,3,4,5,6-hexahydro-1,5-methano-pyrido[1,2-a][1,5]diazocin-8-one (cytisine)

68. Cytisine1,2,3,4,5,6-hexahydro-1,5-methano-pyrido[1,2-a][1,5]diazocin-8-one

69. Hms2096n10

70. Hms2235l06

71. Hms3267d20

72. Hms3414n03

73. Hms3678l21

74. Hms3884l11

75. Hy-n0175

76. Tnp00030

77. Zinc1599730

78. Bdbm50143282

79. Pdsp1_000461

80. S2287

81. Wln: T C666 A Gvn Lm&ttj

82. Akos000276818

83. Akos015833102

84. Ccg-208621

85. Db09028

86. (1r,5s)-1,2,3,4,5,6-hexahydro-1,5-methano-8h-pyrido[1,2a][1,5]diazocin-8-one

87. Ncgc00016463-01

88. Ncgc00016463-02

89. Ncgc00016463-03

90. Ncgc00016463-04

91. Ncgc00017171-01

92. Ncgc00025138-01

93. Ncgc00025138-02

94. Ncgc00179513-01

95. Ac-34317

96. As-19539

97. Bc164343

98. Cas-485-35-8

99. Cs-0007888

100. Sw219952-1

101. Cytisine, >=99.0% (hplc), >=99%

102. 485c358

103. Q417343

104. Brd-k74186897-001-02-5

105. Brd-k74186897-001-04-1

106. Brd-k74186897-001-13-2

107. F9994-5373

108. Z2582785591

109. 1,2-a][1,5]diazocin-8-one, 1,2,3,4,5,6-hexahydro-

110. 1,2-a][1,5]diazocin-8-one, 1,2,3,4,5,6-hexahydro-, (1r)-

111. (1r,9s)-7,11-diazatricyclo[7.3.1.0~2,7~]trideca-2,4-dien-6-one

112. 1,2-a][1,5]diazocin-8-one, 1,2,3,4,5,6-hexahydro-, (1r-cis)-

113. (1r,5s)-1,2,3,4,5,6-hexahydro-1,5-methano-pyrido[1,2-a][1,5]diazocin-8-one

114. (1r,5s)-1,2,3,4,5,6-hexahydro-1,5-methano-8h-pyrido-(1,2-a)(1,5)diazocin-8-one

115. (1r,5s)-1,2,3,4,5,6-hexahydro-8h-1,5-methanopyrido(1,2-a)(1,5)diazocin-8-one (cytisine)

116. 115051-74-6

2.4 Create Date

2005-07-11

3 Chemical and Physical Properties

Molecular Formula	C₁₁H₁₄N₂O
Molecular Weight	190.24 g/mol
XLogP3	0.2
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	2
Rotatable Bond Count	0
Exact Mass	190.110613074 g/mol
Monoisotopic Mass	190.110613074 g/mol
Topological Polar Surface Area	32.3 Å²
Heavy Atom Count	14
Formal Charge	0
Complexity	332
Isotope Atom Count	0
Defined Atom Stereocenter Count	2
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Therapeutic Uses

Nicotine/antagonists and inhibitors

National Library of Medicine's Medical Subject Headings online file (MeSH, 2009)

/Cytisine is indicated for/ treatment of chronic nicotinism. It is particularly appropriate for treatment of risk groups of smokers with health problems on the part of the cardiovascular and respiratory systems, as well as smokers professionally subjected to tension and stress that are predisposed to seek a "false comfort" in nicotine or other drugs causing dependence. /NOT included in US product label/

Sopharma AD; Patient Information for Tabex tablets (2006).

/Investigators/ conducted a single-center, randomized, double-blind, placebo-controlled trial. Participants were randomly assigned to receive cytisine or matching placebo for 25 days; participants in both groups received a minimal amount of counseling during the study. The primary outcome measure was sustained, biochemically verified smoking abstinence for 12 months after the end of treatment. Of 1542 adult smokers screened, 740 were enrolled and 370 were randomly assigned to each study group. The rate of sustained 12-month abstinence was 8.4% (31 participants) in the cytisine group as compared with 2.4% (9 participants) in the placebo group (difference, 6.0 percentage points; 95% confidence interval (CI), 2.7 to 9.2; P=0.001). The 7-day point prevalence for abstinence at the 12-month follow-up was 13.2% in the cytisine group versus 7.3% in the placebo group (P=0.01). Gastrointestinal adverse events were reported more frequently in the cytisine group (difference, 5.7 percentage points; 95% CI, 1.2 to 10.2). ...

PMID:21991893 West R et al; N Engl J Med 365: 1193-1200 (2011)

Cytisine, a natural plant alkaloid, has been marketed in Central and Eastern Europe for over 40 years for the clinical management of smoking cessation. Despite the fact that cytisine has been used by millions of smokers, its characteristics have not been reviewed in scientific literature in English, and presently existing clinical studies on its effectiveness and safety are insufficient to warrant licensing by modern standards. Understanding of the mechanism of cytisine action as a smoking cessation aid provides a necessary basis for conducting clinical trials to confirm its efficacy as an optimal antismoking therapy. ... /Investigators/ present a review of current knowledge about the pharmacokinetics, pharmacodynamics, toxicity, therapeutic efficacy and safety of cytisine, and about its derivatives that are under development. Recent pharmacological research has elucidated that the drug is a low efficacy partial agonist of alpha4beta2 nicotinic acetylcholine receptors, which are believed to be central to the effect of nicotine (NIC) on the reward pathway. The drug reduces the effects of NIC on dopamine release in the mesolimbic system when given alone, while simultaneously attenuating NIC withdrawal symptoms that accompany cessation attempts. Clinical studies on cytisine as a smoking cessation aid have demonstrated that the drug is effective and safe. /The/ recent uncontrolled trial has shown that a 12-month carbon monoxide-verified continuous abstinence rate following a standard course of treatment with cytisine with minimal behavioral support is similar (13.8%; N = 436) to that observed following treatment with NIC replacement therapy. Since cytisine exhibits a desirable pharmacological profile which makes it an attractive smoking cessation drug, it should be advanced to randomized clinical trials. However, more detailed preclinical studies on its pharmacokinetics and safety profile are required.

PMID:17220536 Tutka P, Zatonski W; Pharmacol Rep 58 (6): 777-98 (2006)

4.2 Drug Warning

/Contraindications for cytisine include:/ Advanced atherosclerosis, some forms of schizophrenia, pheochromocytome, conditions connected with severe impairment of the cardiovascular system and malignant hypertension.

Sopharma AD; Patient Information for Tabex tablets (2006).

The following adverse effects are rather often observed at the beginning of /Cytisine/ treatment: changes in both taste and appetite, dryness in the mouth, headache, irritability, nausea, constipation, tachycardia, light elevation of the arterial pressure.

Sopharma AD; Patient Information for Tabex tablets (2006).

The drug should be administered carefully to patients with exacerbated peptic ulcer. After completing the treatment course, the patients should refrain from smoking...

Sopharma AD; Patient Information for Tabex tablets (2006).

The physicians should warn the patients that the simultaneous administration of the drug and smoking could lead to aggravated adverse effects of nicotine (nicotine intoxication). The drug should be used in all cases when the patient has a honest and firm intention to give up smoking.

Sopharma AD; Patient Information for Tabex tablets (2006).

For more Drug Warnings (Complete) data for CYTISINE (8 total), please visit the HSDB record page.

4.3 Drug Indication

Indicated for use in smoking cessation.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Various models have been run where the affinity of nAChR agonists to the receptor subtype are tested to help identify the molecules, groups and steric conformation that are vital to greater affinity. By using a nAChR muscle receptor subtype (1)21 model the following results were obtained: anatoxin > epibatidine > acetylcholine > DMPP >> CYTISINE > pyrantel > nicotine > coniine > tubocurare > lobeline, where anatoxin had the highest activity efficacy and tubocurare the lowest. Acetylcholine on the other hand induced a much longer opening time of the receptor though anatoxin is more potent. The results suggest that anatoxin derivatives would be helpful in understanding structure-activity relationships (SAR) for muscle nAChRs (Cooper et al., 1996).

5.2 ATC Code

N - Nervous system

N07 - Other nervous system drugs

N07B - Drugs used in addictive disorders

N07BA - Drugs used in nicotine dependence

N07BA04 - Cytisinicline

5.3 Absorption, Distribution and Excretion

Volume of Distribution

Oral: 6.2 l/kg Oral (5 mg/kg; tested in rabbits).

Clearance

Renal: 43 mL/min.

The pharmacokinetic behavior of cytisine was studied in mice by means of tritiated cytisine after intravenous and oral administration of a sublethal dose of 2 mg/kg. After oral administration the maximum blood level is reached after 2 hr. The absorption rate is approximately 42%. From the blood level after intravenous administration a half-life of 200 min was calculated. Within 24 hr after intravenous administration 32% and after oral administration 18% of the administered radioactivity was excreted into urine. Following intravenous administration 3% of the dose was found in the feces within 6 hr. Among the examined organs and tissues the highest concentrations were reached in the liver, adrenals and kidneys. In the bile the highest concentration after intravenous administration was 200 times that in the blood.

PMID:6933924 Klocking HP et al; Arch Toxicol Suppl 4: 312-4 (1980)

Experimental study of pharmacokinetics of transdermal system with cytisine in rabbits showed a possibility of controlled intake of the drug over a 4-day period. The two stages of attaining the stationary levels of cytisin concentrations are revealed. The first stage lasted during first 24 hr and the second stage during succeeding 3 days. Using the data on intravenous cytisine injection we found that the stationary concentrations and the rate of cytisine intake in the first stage is twice as large as in the second stage. Thus cytisine can be classed as a short-living drug.

PMID:10650531 Sariev AK et al; Eksp Klin Farmakol 62 (6): 59-61 (1999)

5.4 Biological Half-Life

4.8 hours.

... The absorption rate is approximately 42%. From the blood level after intravenous administration a half-life of 200 min was calculated.

PMID:6933924 Klocking HP et al; Arch Toxicol Suppl 4: 312-4 (1980)

5.5 Mechanism of Action

Cytisine is a low efficacy partial agonist of 4-2 nicotinic acetylcholine receptors. These which are believed to be central to the effect of nicotine (NIC) on the reward pathway and facilitate addiction. Cytisine reduces the effects of NIC on dopamine release in the mesolimbic system when given alone, while simultaneously attenuating NIC withdrawal symptoms that accompany cessation attempts.

Cytisine is an agonist of the cholinoreceptors in the vegetative ganglia and belongs to the group of the gangliostimulating drugs. It excites the nicotine-sensitive cholinoreceptors of the postsynaptic membranes in the vegetative ganglia, chromaffin cells in the molecular part of the suprarenal gland and sinocarotid reflexogenic zone, which results in excitation of the respiratory center, predominantly through the reflexes, simulation of adrenaline release by the medullar part of the suprarenal glands and a rise in the blood pressure. After its absorption in the gastrointestinal tract, cytisine plays the part of a nicotine-substitute substance which decreases the period of interaction between nicotine and the corresponding receptors. This in turn leads to a gradual decrease and interruption of the smokers' psychic and physical nicotine dependence.

Sopharma AD; Patient Information for Tabex tablets (2006).

A family of genes has been identified that encodes subunits of nicotinic acetylcholine receptors (nAChRs) and is expressed in the nervous system. Functional neuronal nAChRs can be expressed in Xenopus oocytes by injection of RNA encoding 1 of 2 different beta-subunits (beta 2, beta 4) in pairwise combination with RNA encoding 1 of 3 different alpha-subunits (alpha 2, alpha 3, alpha 4). We examined the sensitivity of these 6 different alpha- beta-subunit combinations to the nicotinic agonists ACh, nicotine, cytisine, and 1,1-dimethyl-4-phenylpiperazinium (DMPP). Each subunit combination displayed a distinct pattern of sensitivity to these 4 agonists. The alpha 2 beta 2 combination was 5-fold more sensitive to nicotine than to acetylcholine, while the alpha 3 beta 2 combination was 17-fold less sensitive to nicotine than to ACh, and the alpha 3 beta 4 combination was equally sensitive to both nicotine and ACh. nAChRs composed of alpha 2, alpha 3, or alpha 4 in combination with beta 2 were 14-100-fold less sensitive to cytisine than to ACh. In contrast, nAChRs composed of alpha 2, alpha 3, or alpha 4 in combination with beta 4 were 3-17-fold more sensitive to cytisine than to ACh. The alpha 2 beta 2, alpha 3 beta 2, and alpha 3 beta 4 combinations were each equally sensitive to DMPP and ACh, while the alpha 2 beta 4, alpha 4 beta 2, and alpha 4 beta 4 combinations were 4-24-fold less sensitive to DMPP than to ACh. We also demonstrated that these differences are neither a consequence of variation in the relative amounts of RNA injected nor an artifact of oocyte expression. The oocyte system can accurately express ligand-gated ion channels because mouse muscle nAChRs expressed in oocytes display pharmacological properties similar to those reported for these receptors expressed on BC3H-1 cells. We conclude that both the alpha- and the beta-subunits contribute to the pharmacological characteristics of neuronal nAChRs.

PMID:1705971 Luetje CW, Patrick J; J Neurosci. 11(3):837-45 (1991)

Neuronal nicotinic acetylcholine receptors subserve predominantly modulatory roles in the brain, making them attractive therapeutic targets. Natural products provide key leads in the quest for nicotinic receptor subtype-selective compounds. Cytisine, found in Leguminosae spp., binds with high affinity to alpha4beta2* nicotinic receptors. We have compared the effect of C3 and C5 halogenation of cytisine and methylcytisine (MCy) on their interaction with native rat nicotinic receptors. 3-Bromocytisine (3-BrCy) and 3-iodocytisine (3-ICy) exhibited increased binding affinity (especially at alpha7 nicotinic receptors; Ki approximately 0.1 microM) and functional potency, whereas C5-halogenation was detrimental. 3-BrCy and 3-ICy were more potent than cytisine at evoking (3)H dopamine release from striatal slices (EC50 approximately 11 nM), (3)H noradrenaline release from hippocampal slices (EC50 approximately 250 nM), increases in intracellular Ca2+ in PC12 cells and inward currents in Xenopus oocytes expressing human alpha3beta4 nicotinic receptor (EC50 approximately 2 microM). These compounds were also more efficacious than cytisine. C3-halogenation of cytisine is proposed to stabilize the open conformation of the nicotinic receptor but does not enhance subtype selectivity.

PMID:16563372 Abin-Carriquiry JA et al; Eur J Pharmacol. 536(1-2):1-11(2006)

Cytisine, a partial agonist that binds with high affinity to the alpha4beta2 nicotinic acetylcholine receptor...

PMID:21991893 West R et al; N Engl J Med 365: 1193-1200 (2011)

For more Mechanism of Action (Complete) data for CYTISINE (7 total), please visit the HSDB record page.

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Cytisine

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About the Company : Specializing in natural & oncology APIs, we establish R&D and production platforms for new salt, crystal form & synthetic biology research. We cooperate with clients for IND, NDA, ...

Specializing in natural & oncology APIs, we establish R&D and production platforms for new salt, crystal form & synthetic biology research. We cooperate with clients for IND, NDA, ANDA, 505b(2) and P-IV challenges. Exploring macromolecular APIs, we focus on Glycans & polypeptides. Expertise in XDC drugs drives innovative research & payload production. With a global registration platform & international cGMP system, we offer API CMO/CDMO services worldwide. Our strategy combines FDF and APIs. Our labs meet GMP standards with a stable R&D team, over 10 years of experience, we've delivered 20+ successful projects.

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API Reference Price

[{"dataSource":"API Import","activeIngredients":"","year":"2024","qtr":"Q1","strtotime":1711045800,"product":"CYTISINE","address":"2ND FLOOR, SERENE CHAMBERS,,ROAD N","city":"HYDEABAD,TELANGANA","supplier":"SINOLITE INDUSTRIAL CO.,LTD.","supplierCountry":"CHINA","foreign_port":"BEIJING","customer":"LAURUS LABS","customerCountry":"INDIA","quantity":"1.00","actualQuantity":"1","unit":"KGS","unitRateFc":"3600","totalValueFC":"3631","currency":"USD","unitRateINR":"301500","date":"22-Mar-2024","totalValueINR":"301500","totalValueInUsd":"3631","indian_port":"Hyderabad Air","hs_no":"29339990","bill_no":"2700900","productDescription":"API","marketType":"REGULATED MARKET","country":"CHINA","selfForZScoreResived":"Pharma Grade","supplierPort":"BEIJING","supplierAddress":"19D,E,ZHEJIANG MATERIAL INDUSTRIALBUILDING,445 KAIXUAN ROAD,HANGZHOU310021 CHINA China","customerAddress":"2ND FLOOR, SERENE CHAMBERS,,ROAD N"},{"dataSource":"API Import","activeIngredients":"","year":"2024","qtr":"Q2","strtotime":1718562600,"product":"CYTISINE (QTY: 100GMS, VALUE : USD 2550)","address":"PLOT NO.2, MAITRIVIHAR,","city":"HYDERABAD\/ANDHRA PRADESH","supplier":"SICHUAN XIELI PHARMACEUTICAL","supplierCountry":"HONG KONG","foreign_port":"HONG KONG","customer":"AUROBINDO PHARMA LIMITED","customerCountry":"INDIA","quantity":"0.10","actualQuantity":"0.1","unit":"KGS","unitRateFc":"25500","totalValueFC":"2799.2","currency":"USD","unitRateINR":"2336796","date":"17-Jun-2024","totalValueINR":"233679.6","totalValueInUsd":"2799.2","indian_port":"Hyderabad Air","hs_no":"29398000","bill_no":"4033201","productDescription":"API","marketType":"LESS REGULATED MARKET","country":"HONG KONG","selfForZScoreResived":"Pharma Grade","supplierPort":"HONG KONG","supplierAddress":"NO.588, MIDDLE SECTION OF MUDAN AVENUE, TIANPENG TOWN, PENGZHOU CITY,SICHUAN, CHINA China","customerAddress":"PLOT NO.2, MAITRIVIHAR,"},{"dataSource":"API Import","activeIngredients":"","year":"2024","qtr":"Q4","strtotime":1730140200,"product":"CYTISINE","address":"2ND FLOOR, SERENE CHAMBERS,","city":"","supplier":"SICHUAN XIELI PHARMACEUTICAL","supplierCountry":"CHINA","foreign_port":"BEIJING","customer":"LAURUS LABS","customerCountry":"INDIA","quantity":"1.50","actualQuantity":"1.5","unit":"KGS","unitRateFc":"4000","totalValueFC":"6065.9","currency":"USD","unitRateINR":"339800","date":"29-Oct-2024","totalValueINR":"509700","totalValueInUsd":"6065.9","indian_port":"Hyderabad Air","hs_no":"29339990","bill_no":"6404910","productDescription":"API","marketType":"REGULATED MARKET","country":"CHINA","selfForZScoreResived":"Pharma Grade","supplierPort":"BEIJING","supplierAddress":"NO.588, MIDDLE SECTION OF MUDAN AVE NUE, TIANPENG TOWN, PENGZHOU, SICHU AN, CHINA China","customerAddress":"2ND FLOOR, SERENE CHAMBERS,"}]