IBANDRONATE SODIUM ANHYDROUS

Details

Stereochemistry	ACHIRAL
Molecular Formula	C9H22NO7P2.Na
Molecular Weight	341.2108
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure of IBANDRONATE SODIUM ANHYDROUS

Structure Search

SMILES

[Na+].CCCCCN(C)CCC(O)(P(O)(O)=O)P(O)([O-])=O

InChI

InChIKey=LXLBEOAZMZAZND-UHFFFAOYSA-M

InChI=1S/C9H23NO7P2.Na/c1-3-4-5-7-10(2)8-6-9(11,18(12,13)14)19(15,16)17;/h11H,3-8H2,1-2H3,(H2,12,13,14)(H2,15,16,17);/q;+1/p-1

HIDE SMILES / InChI

Molecular Formula	Na
Molecular Weight	22.9898
Charge	1
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	C9H22NO7P2
Molecular Weight	318.221
Charge	-1
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.drugs.com/dosage/ibandronate.html

Ibandronic acid (INN) or ibandronate sodium (USAN) is a potent bisphosphonate drug developed by Hoffman La Roche and used in the prevention and treatment of osteoporosis and metastasis-associated skeletal fractures in people with cancer. Ibandronate is indicated for the treatment and prevention of osteoporosis in post-menopausal women. In May 2003, the U.S. Food and Drug Administration (FDA) approved Ibandronate as a daily treatment for post-menopausal osteoporosis. The basis for this approval was a three-year, randomized, double-blind, placebo-controlled trial women with post-menopausal osteoporosis. Every participant also received daily oral doses of calcium and 400IUs [international units] of vitamin D. At the study's conclusion, both doses significantly reduced the occurrence risk of new vertebral fractures by 50–52 percent when compared to the effects of the placebo drug. Ibandronate is efficacious for the prevention of metastasis-related bone fractures in multiple myeloma, breast cancer, and certain other cancers. In 2008, the U.S Food and Drug Administration (FDA) issued a communication warning of the possibility of severe and sometimes incapacitating bone, joint and/or muscle pain.[4] A study conducted by the American Society of Bone and Mineral Research concluded that long-term use of bisphosphonates, including Boniva, may increase the risk of a rare but serious fracture of the femur. Ibandronic acid is marketed under the trade names Boniva in the USA, Bondronat in Europe, Bonviva in Asia, Ibandrix in Ecuador and Bondrova in Bangladesh.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Mevalonate Pathway 3 Target ID: WP3104 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16620148	Inhibitor 8297

Conditions

Condition	Modality	Highest Phase	Product
Postmenopausal osteoporosis 59 Sources: https://clinicaltrials.gov/ct2/show/NCT02604836	Primary	Approved 8429	Boniva Approved Use Unknown
Osteoporosis 97 Sources: https://www.drugs.com/cdi/ibandronate.html	Primary	Approved 8429	Boniva Approved Use Unknown
Bone cancer 3 Sources: https://clinicaltrials.gov/ct2/show/NCT02561039	Primary	Approved 8429	Boniva Approved Use Directions: Acne Clearing Cleanser Acne Clearing Tonic Acne Clearing Treatment 101

C_max

Value	Dose	Co-administered	Analyte	Population
90.64 ng/mL EXPERIMENT https://synapse.koreamed.org/Synapse/Data/PDFData/1179TCP/tcp-22-22.pdf	150 mg single, oral dose: 150 mg route of administration: Oral experiment type: SINGLE co-administered:		IBANDRONIC ACID plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
549.24 ng × h/mL EXPERIMENT https://synapse.koreamed.org/Synapse/Data/PDFData/1179TCP/tcp-22-22.pdf	150 mg single, oral dose: 150 mg route of administration: Oral experiment type: SINGLE co-administered:		IBANDRONIC ACID plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
32.38 h EXPERIMENT https://synapse.koreamed.org/Synapse/Data/PDFData/1179TCP/tcp-22-22.pdf	150 mg single, oral dose: 150 mg route of administration: Oral experiment type: SINGLE co-administered:		IBANDRONIC ACID plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

Doses

Dose	Population	Adverse events
100 mg 1 times / month multiple, oral Dose: 100 mg, 1 times / month Route: oral Route: multiple Dose: 100 mg, 1 times / month Sources: https://pubmed.ncbi.nlm.nih.gov/28389932	unhealthy, 55–74 years n = 183 Health Status: unhealthy Condition: osteoporosis Age Group: 55–74 years Sex: M+F Population Size: 183 Sources: https://pubmed.ncbi.nlm.nih.gov/28389932	Sources: https://pubmed.ncbi.nlm.nih.gov/28389932
2.5 mg 1 times / day multiple, oral Recommended Dose: 2.5 mg, 1 times / day Route: oral Route: multiple Dose: 2.5 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2006/021858s000_MedR_P1.pdf Page: p. 24	unhealthy, adult n = 465 Health Status: unhealthy Condition: postmenopausal osteoporosis Age Group: adult Sex: F Population Size: 465 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2006/021858s000_MedR_P1.pdf Page: p. 24	Disc. AE: Gastrointestinal disorder (NOS), Musculoskeletal disorder NOS... AEs leading to discontinuation/dose reduction: Gastrointestinal disorder (NOS) (4%) Musculoskeletal disorder NOS (1%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2006/021858s000_MedR_P1.pdf Page: p. 24
2 mg 1 times / 2 months multiple, intravenous Dose: 2 mg, 1 times / 2 months Route: intravenous Route: multiple Dose: 2 mg, 1 times / 2 months Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2006/021858s000_MedR_P1.pdf Page: p. 24	unhealthy, adult n = 442 Health Status: unhealthy Condition: postmenopausal osteoporosis Age Group: adult Sex: F Population Size: 442 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2006/021858s000_MedR_P1.pdf Page: p. 24	Disc. AE: Gastrointestinal disorder (NOS), Musculoskeletal disorder NOS... AEs leading to discontinuation/dose reduction: Gastrointestinal disorder (NOS) (4%) Musculoskeletal disorder NOS (2%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2006/021858s000_MedR_P1.pdf Page: p. 24
3 mg 1 times / 3 months multiple, intravenous Dose: 3 mg, 1 times / 3 months Route: intravenous Route: multiple Dose: 3 mg, 1 times / 3 months Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2006/021858s000_MedR_P1.pdf Page: p. 24	unhealthy, adult n = 458 Health Status: unhealthy Condition: postmenopausal osteoporosis Age Group: adult Sex: F Population Size: 458 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2006/021858s000_MedR_P1.pdf Page: p. 24	Disc. AE: Gastrointestinal disorder (NOS), Musculoskeletal disorder NOS... AEs leading to discontinuation/dose reduction: Gastrointestinal disorder (NOS) (4%) Musculoskeletal disorder NOS (2%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2006/021858s000_MedR_P1.pdf Page: p. 24
150 mg 1 times / month multiple, oral Dose: 150 mg, 1 times / month Route: oral Route: multiple Dose: 150 mg, 1 times / month Sources: https://clinicaltrials.gov/ct2/show/NCT00545051	unhealthy n = 70 Health Status: unhealthy Condition: Osteoporosis Sex: F Population Size: 70 Sources: https://clinicaltrials.gov/ct2/show/NCT00545051	Other AEs: Agranulocytosis, Acute pancreatitis... Other AEs: Agranulocytosis (serious, 1 patient) Acute pancreatitis (serious, 1 patient) Acute pyelonephritis (serious, 1 patient) Sepsis (serious, 1 patient) Concussion (serious, 1 patient) Poisoning (serious, 1 patient) Follicle centre lymphoma diffuse small cell lymphoma (serious, 1 patient) Malignant tongue neoplasm (serious, 1 patient) Transient ischaemic attack (serious, 1 patient) Pulmonary embolism (serious, 1 patient) Deep vein thrombosis (serious, 2 patients) Influenza (below serious, 4 patients) Arthralgia (below serious, 8 patients) Rheumatoid arthritis (below serious, 4 patients) Sources: https://clinicaltrials.gov/ct2/show/NCT00545051
150 mg 1 times / month multiple, oral Dose: 150 mg, 1 times / month Route: oral Route: multiple Dose: 150 mg, 1 times / month Sources: https://clinicaltrials.gov/ct2/show/NCT00397839	unhealthy n = 86 Health Status: unhealthy Condition: Osteoporosis Sex: M Population Size: 86 Sources: https://clinicaltrials.gov/ct2/show/NCT00397839	Other AEs: Death, Syncope... Other AEs: Death (serious, 1 patient) Syncope (serious, 2 patients) Pneumonia (serious, 1 patient) Retinal detachment (serious, 1 patient) Rectal haemorrhage (serious, 1 patient) Pneumoconiosis (serious, 1 patient) Nasopharyngitis (below serious, 7 patients) Nausea (below serious, 4 patients) Upper respiratory tract infection (below serious, 3 patients) Sources: https://clinicaltrials.gov/ct2/show/NCT00397839

AEs

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 1587 substrate 1737	inhibitor 1767 substrate 1037	inhibitor 1852 substrate 1217	inhibitor 1612

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 1524 CYP2A6 707 CYP2C19 1478 CYP2E1 882	CYP1A2 1054 CYP2A6 543 CYP2C19 991 CYP2E1 667

Drug as perpetrator

Target	Modality	Activity
CYP1A2 1692	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2003/21-455_Boniva_biopharmr.pdf#page=5 Page: 5.0	no
CYP2A6 739	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2003/21-455_Boniva_biopharmr.pdf#page=5 Page: 5.0	no
CYP2C19 1553	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2003/21-455_Boniva_biopharmr.pdf#page=5 Page: 5.0	no
CYP2C9 1819	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2003/21-455_Boniva_biopharmr.pdf#page=5 Page: 5.0	no
CYP2D6 1891	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2003/21-455_Boniva_biopharmr.pdf#page=5 Page: 5.0	no
CYP2E1 970	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2003/21-455_Boniva_biopharmr.pdf#page=5 Page: 5.0	no
CYP3A4 1925	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2003/21-455_Boniva_biopharmr.pdf#page=5 Page: 5.0	no

Drug as victim

Target	Modality	Activity
CYP1A2 1054	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2003/21-455_Boniva_biopharmr.pdf#page=11 Page: 11.0	no
CYP2A6 543	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2003/21-455_Boniva_biopharmr.pdf#page=11 Page: 11.0	no
CYP2C19 991	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2003/21-455_Boniva_biopharmr.pdf#page=11 Page: 11.0	no
CYP2C9 1037	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2003/21-455_Boniva_biopharmr.pdf#page=11 Page: 11.0	no
CYP2D6 1217	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2003/21-455_Boniva_biopharmr.pdf#page=11 Page: 11.0	no
CYP2E1 667	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2003/21-455_Boniva_biopharmr.pdf#page=11 Page: 11.0	no
CYP3A4 1737	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2003/21-455_Boniva_biopharmr.pdf#page=11 Page: 11.0	no

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 1647	inhibitor 1626 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2003/21-455_Boniva_pharmr_P1.pdf#page=4 Page: 4.0

Sourcing

Vendor/Aggregator	ID	URL
3B Scientific (Wuhan) Corp	3B2-1493	http://www.3bsc.com/index/pro_info.php?id=55209
AA Blocks	AA000AF6	http://www.aablocks.com/goods/Goods/detail?id=AA000AF6
AEchem Scientific Corp., USA	AE032312	http://www.aechemsc.com/info_products/AE032312.php
AHH Chemical co.,ltd	MT-01142	http://www.ahhchemical.com/product/MT-01142.html
AK Scientific, Inc. (AKSCI)	71724	http://www.aksci.com/item_detail.php?cat=71724
Acadechem	ACDS-026262	http://www.acadechemical.com/product/100961
Achemtek	0104-008135	http://www.achemtek.com/114084-78-5
Angene	AGN-PC-04XVIP	http://www.angenechemical.com/productshow/AGN-PC-04XVIP.html
Aurora Fine Chemicals LLC	A13.112.890	http://online.aurorafinechemicals.com/info?ID=A13.112.890
Aurum Pharmatech LLC	M-1207	http://www.Aurumpharmatech.com/Product/ProductDetails/M_1207
AvaChem Scientific	2445A	http://www.avachem.com/productSearch.asp?2445A
BLD Pharm	BD17613	http://www.bldpharm.com/products/114084-78-5.html
BioChemPartner	BCP13798	http://www.biochempartner.com/114084-78-5-BCP13798
BioSynth	J-003052	https://www.biosynth.com/en/products/all-products/products/J-003052.html
Boerchem	BC219057	http://www.boerchem.com/?product_36883.html
CSNpharm	CSN12493	https://www.csnpharm.com/products/ibandronate.html
Chem Scene	CS-2726	http://www.chemscene.com/114084-78-5.html
ChemMol	30108986	http://www.chemmol.com/chemmol/30108986.html
ChemMol	44005823	http://www.chemmol.com/chemmol/44005823.html
ChemMol	49409545	http://www.chemmol.com/chemmol/49409545.html
ChemMol	81411772	http://www.chemmol.com/chemmol/81411772.html
Chemspace	CSSB00000036762	https://chem-space.com/CSSB00000036762
Clearsynth	CS-O-01646	http://www.clearsynth.com/en/CSO01646.html
Clearsynth	CS-BU-00048	https://www.clearsynth.com/en/CSBU00048.html
Clearsynth	CS-O-30604	https://www.clearsynth.com/en/CSO30604.html
Finetech	FT-0670253	http://www.finetechnology-ind.com/prod/detail/pub/1130899-41-0.html
Finetech	FT-0602640	http://www.finetechnology-ind.com/prod/detail/pub/114084-78-5.html
Hefei Hirisun Pharmatech Co., Ltd	HR130939	http://hirisunpharm.com/114084-78-5.html
Matrix Scientific	100579	https://www.matrixscientific.com/100579.html
MedChem Express	HY-B0515A	https://www.medchemexpress.com/Ibandronic-acid.html
MuseChem	I000530	https://www.musechem.com/product/I000530.html
OChem	7534	http://www.ocheminc.com/index.php?act=psearch&pid=084I785
Sinfoo Biotech	S010605	http://www.sinfoobiotech.com/product/1014003
Smolecule	S594667	https://www.smolecule.com/products/s594667
THE BioTek	bt-300824	https://www.thebiotek.com/product/others/bt-300824
Yuhao Chemical	RT16287	http://www.chemyuhao.com/114084-78-5.html
abcr GmbH	AB506647	http://www.abcr.com/shop/en/AB506647
iChemical	EBD38131	http://www.ichemical.com/chemicals/cas-114084-78-5

PubMed

Title	Date	PubMed
[TNF-alpha secretion by human macrophage-like cells in response to wear particles and its modification by drugs].	1999 May	10413987
Should bisphosphonates be the treatment of choice for metastatic bone disease?	2001 Aug	11544574
Structure-activity relationships for inhibition of farnesyl diphosphate synthase in vitro and inhibition of bone resorption in vivo by nitrogen-containing bisphosphonates.	2001 Feb	11160603
Bisphosphonates in the treatment of metastatic breast cancer.	2001 Oct	12013536
The present and future role of bisphosphonates in the management of patients with breast cancer.	2002	11879556
Direct effects of bisphosphonates on breast cancer cells.	2002	11879555
Bisphosphonates for breast cancer.	2002	11869664
Bisphosphonates for prevention of postmenopausal osteoporosis.	2002 Feb	11894721
Association between pharmacokinetics of oral ibandronate and clinical response in bone mass and bone turnover in women with postmenopausal osteoporosis.	2002 Jan	11792604
Bisphosphonates for cancer patients: why, how, and when?	2002 Jul	12136223
Effects of treatment with ibandronate on bone mass, architecture, biomechanical properties, and bone concentration of ibandronate in ovariectomized aged rats.	2002 Oct	12375334
The effect of the bisphosphonate ibandronate on breast cancer metastasis to visceral organs.	2002 Oct	12353814
Effect of transplantation on bone: osteoporosis after liver and multivisceral transplantation.	2002 Sep	12270405
Safety and efficacy of the new bisphosphonate ibandronate in the management of bone metastasis following rapid infusion.	2002 Sep-Oct	12494878
New insights into the molecular mechanisms of action of bisphosphonates.	2003	14529538
Breast cancer patients with bone metastases are characterised by increased levels of nonisomerised type I collagen fragments.	2003	12818000
The efficacy of 48-week oral ibandronate treatment in postmenopausal osteoporosis when taken 30 versus 60 minutes before breakfast.	2003 Apr	12689686
Injectable bisphosphonates in the treatment of postmenopausal osteoporosis.	2003 Aug	14661816
Oral weekly ibandronate prevents bone loss in postmenopausal women.	2003 Aug	12859697
Injectable drug dampens bone loss.	2003 Dec	14679970
[How to treat tumor-induced hypercalcemia].	2003 Dec 15	15008469
Antagonistic effects of different classes of bisphosphonates in osteoclasts and macrophages in vitro.	2003 Feb	12568397
Antitumor effects of bisphosphonates.	2003 Feb 1	12548584
Pamidronate is superior to ibandronate in decreasing bone resorption, interleukin-6 and beta 2-microglobulin in multiple myeloma.	2003 Jan	12631257
The diagnosis and management of hypercalcaemia.	2003 Jan	12625112
The bisphosphonate ibandronate stimulates reverse cholesterol transport out of monocytoid cells by enhanced ABCA1 transcription.	2003 Jul 18	12849976
Bisphosphonates antagonise bone growth factors' effects on human breast cancer cells survival.	2003 Jul 7	12838321
Ibandronate: a potent new bisphosphonate in the management of postmenopausal osteoporosis.	2003 Jun	12846348
Oral ibandronate: changes in markers of bone turnover during adequately dosed continuous and weekly therapy and during different suboptimally dosed treatment regimens.	2003 Jun	12810176
Therapy of osteoporosis in patients with Crohn's disease: a randomized study comparing sodium fluoride and ibandronate.	2003 Mar 15	12641503
Ibandronate: new options in the treatment of osteoporosis.	2003 Nov	14702133
Bisphosphonates in children with bone diseases.	2003 Nov 20	14631923
Intermittent intravenous ibandronate injections reduce vertebral fracture risk in corticosteroid-induced osteoporosis: results from a long-term comparative study.	2003 Oct	14610641
The renal effects of minimally nephrotoxic doses of ibandronate and zoledronate following single and intermittent intravenous administration in rats.	2003 Sep 30	12965119
Treatment of idiopathic hyperphosphatasia with intensive bisphosphonate therapy.	2004 May	15068492
Decreased levels of osteopontin and bone sialoprotein II are correlated with reduced proliferation, colony formation, and migration of GFP-MDA-MB-231 cells.	2004 May	15067347
Daily and intermittent oral ibandronate normalize bone turnover and provide significant reduction in vertebral fracture risk: results from the BONE study.	2004 Oct	15071723

Patents

Sample Use Guides

In Vivo Use Guide

Oral: 150 mg orally once a month on the same day each month IV Injection: 3 mg by IV injection over 15 to 30 seconds every three months.

Route of Administration: Other

In Vitro Use Guide

Cells were cultivated in cell culture flasks at 37_Cand5%CO2. The culture media were as recommended by the American Type Culture Collection (ATCC) for MDA-MB-231 breast cancer DMEM (Sigma-Aldrich, St. Louis, MO, USA), which contained 10% fetal calf serum (FCS); PC-3 prostate carcinoma DMEM-F12 (Sigma-Aldrich) with 10% FCS. MG-63 and U2-OS osteosarcoma were cultured in AlphaMEM (Biochrom, Berlin, Germany) medium containing 10% FBS. For the HMC1.1 cell line, we used Iscove’s Modified Dulbecco’s Medium (IMDM; Thermo Fisher Scientific, Waltham, MA) supplemented with 260 nM thioglycerol (Sigma-Aldrich) and20%fetal bovine serum (FBS). All culture media contained 10 mg/mL gentamycin (Sigma-Aldrich). To guarantee optimal growth, cells were split two times a week and reseeded at a density of 2-5 x 105 cells/mL. One day after splitting, 32 mMsimvastatin (Sigma-Aldrich) or 150 mM ibandronate (Sigma-Aldrich) were added to the culture medium for 72 hours. This is the dose that attenuated cell proliferation with a half maximal effect. NADP/NADPH analyses were performed directly in 96-well culture plates after 24 or 48 hours

Substance Class	Chemical Created by `admin` on `Sat Dec 16 05:03:49 GMT 2023` Edited by `admin` on `Sat Dec 16 05:03:49 GMT 2023`
Record UNII	23Y0B94E49
Record Status	`Validated (UNII)`
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Name

Type

Language

IBANDRONATE SODIUM ANHYDROUS

Common Name

English

BONDRONAT

Brand Name

English

Ibandronate sodium [WHO-DD]

Common Name

English

BONVIVA

Brand Name

English

SODIUM IBANDRONATE ANHYDROUS

Common Name

English

PHOSPHONIC ACID, (1-HYDROXY-3-(METHYLPENTYLAMINO)PROPYLIDENE)BIS-, MONOSODIUM SALT

Common Name

English

IBANDRONIC ACID SODIUM SALT [MI]

Common Name

English

Code System Code Type Description

CAS

138844-81-2