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Lr-103

Lr-103

Synopsis, Chemistry

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Also known as: Lr-103, 156316-85-7, 2900i92z36, (24s)-1alpha,24-dihydroxyvitamin d2 / (24s)-1alpha,24-dihydroxyergocalciferol, (5z,7e,22e)-(1s,3r,24s)-9,10-seco-5,7,10(19),22-ergostatetraene-1,3,24-triol, Unii-2900i92z36

Molecular Formula

C₂₈H₄₄O₃

Molecular Weight

428.6 g/mol

InChI Key

ODZFJAXAEXQSKL-WRJREGAQSA-N

FDA UNII

2900I92Z36

LR-103 is a naturally occurring D-hormone that is produced by the kidneys from vitamin D. LR-103 is one of the D-hormones produced from Hectorol. It is developed for the treatment of secondary hyperparathyroidism in patients with chronic kidney disease (CKD). Studies have shown LR-103 has the same potency as calcitriol, but much lower toxicity.

1 2D Structure

Lr-103

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(1R,3S,5Z)-5-[(2E)-2-[(1R,3aS,7aR)-1-[(E,2R,5S)-5-hydroxy-5,6-dimethylhept-3-en-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylidenecyclohexane-1,3-diol

2.1.2 InChI

InChI=1S/C28H44O3/c1-18(2)28(6,31)15-13-19(3)24-11-12-25-21(8-7-14-27(24,25)5)9-10-22-16-23(29)17-26(30)20(22)4/h9-10,13,15,18-19,23-26,29-31H,4,7-8,11-12,14,16-17H2,1-3,5-6H3/b15-13+,21-9+,22-10-/t19-,23-,24-,25+,26+,27-,28-/m1/s1

2.1.3 InChI Key

ODZFJAXAEXQSKL-WRJREGAQSA-N

2.1.4 Canonical SMILES

CC(C)C(C)(C=CC(C)C1CCC2C1(CCCC2=CC=C3CC(CC(C3=C)O)O)C)O

2.1.5 Isomeric SMILES

C[C@H](/C=C/[C@](C)(C(C)C)O)[C@H]1CC[C@@H]\2[C@@]1(CCC/C2=C\C=C/3\C[C@H](C[C@@H](C3=C)O)O)C

2.2 Other Identifiers

2.2.1 UNII

2900I92Z36

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 1,24(s)-dihydroxyvitamin D2

2. 1,24-dihydroxyvitamin D2

3. 1alpha,24(s)(oh)2d2

4. 1alpha,24(s)-dihydroxyvitamin D2

5. Lr-103

2.3.2 Depositor-Supplied Synonyms

1. Lr-103

2. 156316-85-7

3. 2900i92z36

4. (24s)-1alpha,24-dihydroxyvitamin D2 / (24s)-1alpha,24-dihydroxyergocalciferol

5. (5z,7e,22e)-(1s,3r,24s)-9,10-seco-5,7,10(19),22-ergostatetraene-1,3,24-triol

6. Unii-2900i92z36

7. Lmst03010062

8. 1alpha,24(s)-dihydroxyergocalciferol

9. Schembl3026089

10. Lr 103 [who-dd]

11. Dtxsid801015488

12. Zinc4791507

13. Db06117

14. (1alpha,3beta,5z,7e,22e,24s)-9,10-secoergosta-5,7,10(19),22-tetraene-1,3,24-triol

15. 1.alpha.,24s-dihydroxyvitamin D2

16. 1.alpha.,24(s)-dihydroxyergocalciferol

17. Q27254357

18. (1.alpha.,3.beta.,5z,7e,22e,24s)-9,10-secoergosta-5,7,10(19),22-tetraene-1,3,24-triol

19. 9,10-secoergosta-5,7,10(19),22-tetraene-1,3,24-triol,(1.alpha.,3.beta.,5z,7e,22e)-

2.4 Create Date

2006-08-30

3 Chemical and Physical Properties

Molecular Formula	C₂₈H₄₄O₃
Molecular Weight	428.6 g/mol
XLogP3	5.1
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	5
Exact Mass	428.32904526 g/mol
Monoisotopic Mass	428.32904526 g/mol
Topological Polar Surface Area	60.7 Å²
Heavy Atom Count	31
Formal Charge	0
Complexity	760
Isotope Atom Count	0
Defined Atom Stereocenter Count	7
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	3
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Indication

Investigated for use/treatment in parathyroid disorders.

5 Pharmacology and Biochemistry

5.1 Pharmacology

LR-103 is effective in normalizing serum calcium and PTH levels without causing hypercalcemia. Importantly, LR-103 also normalized bone abnormalities consequent to SHPT and active vitamin D deficiency.