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Zoledronic Acid

HCID 68740
노트반응
기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
부분 구조 검색유사 구조 찾기

기본 정보

CAS
118072-93-8
표준 SMILES
O=P(O)(O)C(O)(Cn1ccnc1)P(=O)(O)O
InChIKey
XRASPMIURGNCCH-UHFFFAOYSA-N
분자식
C5H10N2O7P2
평균 분자량
272.09 g/mol
단동위원소 질량
271.99632392

개요

Zoledronic acid is an imidazole compound having a 2,2-bis(phosphono)-2-hydroxyethane-1-yl substituent at the 1-position. It has a role as a bone density conservation agent. It is a member of imidazoles and a 1,1-bis(phosphonic acid).

이름 및 식별자

우선 이름
Zoledronic Acid
IUPAC
(1-hydroxy-2-imidazol-1-yl-1-phosphonoethyl)phosphonic acid
영어명
Zoledronic acid
분자식
C5H10N2O7P2
분자량
272.09

이름 및 동의어

Zoledronic acid118072-93-8ZoledronateZometaReclastAclasta(1-Hydroxy-2-imidazol-1-ylethylidene)diphosphonic acidZoledronic Acid AnhydrousAnhydrous Zoledronic AcidCGP 42446DTXSID004266870HZ18PH24
이름 더 보기
ZoledronicZolidronic AcidZoledronic Acid APIOrazolBPH 91
Phosphonic acid, [1-hydroxy-2-(1H-imidazol-1-yl)ethylidene]bis-ZOL 446(1-hydroxy-2-(1H-imidazol-1-yl)ethylidene)bisphosphonic acidNSC-721517[1-hydroxy-2-(1H-imidazol-1-yl)-1-phosphonoethyl]phosphonic acidPhosphonic acid, (1-hydroxy-2-(1H-imidazol-1-yl)ethylidene)bis-Zoledronic Acid ActavisDTXCID8022668

데이터베이스 식별자

CAS
118072-93-8
PubChem CID
68740
DTXSID
DTXSID0042668
ChEMBL
CHEMBL4303669、CHEMBL924
ChEBI
CHEBI:46557
UNII
70HZ18PH24
EC Number
871-741-2
Nikkaji
J556.181G

물성

구조 계산 물성

XLogP
-4.3
극성 표면적
153 Ų
수소 결합 공여자 수
5
수소 결합 수용자 수
8
회전 가능 결합 수
4
무거운 원자 수
16
형식 전하
0
복잡도
327

실험 및 물리화학적 성질

Drugs · 2건

Pharmaceuticals -> Listed in ZINC15

Pharmaceuticals

LogP-4.2
Solubility · 2건

Sparingly soluble

3.27e+00 g/L

Human Drugs · 6건

Breast Feeding; Lactation; Bisphosphonates; Bone Density Conservation Agents; Diphosphonates;

FDA approved drugs -> Active ingredient

EMA approved medicines: Human medicine

EMA approved medicines: Human medicine

EMA approved medicines: Human medicine

EMA approved medicines: Human medicine

Physical DescriptionSolid

물리화학적 성질

녹는점
193 · 193-2040C (dec)
끓는 점
764 · 764.0±70.0 °C(Predicted)
밀도
2.13 · 2.13±0.1 g/cm3(Predicted)
저장 조건
Sealed in dry,Room Temperature
용해도
물에 용해됩니다(최대 2mg/ml).
물리적 상태
고체
산도 계수 (pKa)
1.41 · 1.41±0.10(Predicted)

안전 및 규제

안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.

GHS 분류

GHS Classification · 4건

Warning

H317 (100%): May cause an allergic skin reaction [Warning Sensitization, Skin]

P261, P264+P265, P272, P280, P302+P352, P305+P351+P338, P321, P333+P317, P337+P317, P362+P364, and P501 (click each P-code to see the statement)

The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.

유해성 정보

Hazard Classes and CategoriesSkin Sens. 1 (100%)

독성 정보

Adverse Effects · 1건

The commonly reported adverse reactions include pyrexia, headache, myalgia, pain in extremities, and arthralgia. Significant adverse effects associated with zoledronate include hypocalcemia, secondary hyperparathyroidism, acute phase response (APR), renal injury, atypical femur fractures, osteonecrosis of the jaw (ONJ), atrial fibrillation, and ocular inflammation.

Exposure RoutesIntravenous. Poorly absorbed (oral absorption is about 1% of what intravenous absorption is).
Toxicity Summary · 2건

In the event of toxicity or overdose, no reversal agents are approved by the FDA for this drug. In a case report, a pediatric patient with osteogenesis imperfecta experienced a substantial 15-fold overdose of zoledronate. The patient received 4 mg (0.37 mg/kg) instead of the intended 0.27 mg (0.025 mg/kg) dosage, resulting in severe hypocalcemia and hypophosphatemia, necessitating calcium and phosphorus supplementation with ergocalciferol administration. Despite supportive care and hemodialysis initiation to address electrolyte imbalances and potentially eliminate excess zoledronate, the patient experienced multiple episodes of nonsustained ventricular tachycardia. This case underscores the need for prolonged monitoring and electrolyte supplementation in pediatric Zoledronate overdose cases to address potential complications, including severe hypocalcemia and hypophosphatemia.

화학 및 산업

약리 정보

ATC Code · 4건

M05BA08

M - Musculo-skeletal system

QM - Musculo-skeletal system

M05BA08

Protein BindingZoledronic acid is 23-53% protein bound in plasma.
Pharmacodynamics · 1건

Zoledronic acid is a third generation, nitrogen containing bisphosphonate that inhibits osteoclast function and prevents bone resorption. The therapeutic window is wide as patients are unlikely to suffer severe effects from overdoses and the duration of action is long. Patients should be counselled regarding the risk of electrolyte deficiencies, renal impairment, osteonecrosis of the jaw, atypical femoral fractures, bronchoconstriction, hepatic impairment, hypocalcemia, and embryo-fetal toxicity.

Mechanism of Action · 1건

Bisphosphonates are taken into the bone where they bind to hydroxyapatite. Bone resorption by osteoclasts causes local acidification, releasing the bisphosphonate, which is taken into the osteoclast by fluid-phase endocytosis. Endocytic vesicles become acidified, releasing bisphosphonates into the cytosol of osteoclasts where they act. Osteoclasts mediate resorption of bone. When osteoclasts bind to bone they form podosomes, ring structures of F-actin. Etidronic acid also inhibits V-ATPases in the osteoclast, though the exact subunits are unknown, preventing F-actin from forming podosomes. Disruption of the podosomes causes osteoclasts to detach from bones, preventing bone resorption. Nitrogen containing bisphosphonates such as zoledronate are known to induce apoptosis of hematopoietic tumor cells by inhibiting the components of the mevalonate pathway farnesyl diphosphate synthase, farnesyl diphosphate, and geranylgeranyl diphosphate. These components are essential for post-translational prenylation of GTP-binding proteins like Rap1. The lack of prenylation of these proteins interferes with their function, and in the case of Rap1, leads to apoptosis. zoledronate also activated caspases which further contribute to apoptosis.

Biological Half-LifeZoledronic acid has a terminal elimination half life of 146 hours.
Metabolism/Metabolites · 2건

관련 반응

115건
반응 기록 만들기
HRID 730591 반응식
HRID 730591반응물로uspto-grants-2009_09
HRID 730592 반응식
HRID 730592반응물로uspto-grants-2009_09
HRID 730593 반응식
HRID 730593반응물로uspto-grants-2009_09
HRID 730594 반응식
HRID 730594반응물로uspto-grants-2009_09
HRID 730595 반응식
HRID 730595반응물로uspto-grants-2009_09
HRID 730596 반응식
HRID 730596반응물로uspto-grants-2009_09
HRID 730597 반응식
HRID 730597반응물로uspto-grants-2009_09
HRID 730598 반응식
HRID 730598반응물로uspto-grants-2009_09
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화합물 노트

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이 페이지에서기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
색상
흰색 또는 황백색
안정성
2 · 제공된 대로 구매일로부터 2년 동안 안정적입니다. 증류수 용액은 -20°에서 최대 2개월 동안 보관할 수 있습니다.
InChI
InChI=1S/C5H10N2O7P2/c8-5(15(9,10)11,16(12,13)14)3-7-2-1-6-4-7/h1-2,4,8H,3H2,(H2,9,10,11)(H2,12,13,14)
InChIKey
XRASPMIURGNCCH-UHFFFAOYSA-N
SMILES
C(P(=O)(O)O)(P(=O)(O)O)(O)CN1C=NC=C1

화학적 성질

White Solid

The action of zoledronate on bone tissue is based partly on its affinity for hydroxyapatite, which is part of the mineral matrix of bone. Zoledronate also targets farnesyl pyrophosphate (FPP) synthase. Nitrogen-containing bisphosphonates such as zoledronate appear to act as analogues of isoprenoid diphosphate lipids, thereby inhibiting FPP synthase, an enzyme in the mevalonate pathway. Inhibition of this enzyme in osteoclasts prevents the biosynthesis of isoprenoid lipids (FPP and GGPP) that are essential for the post-translational farnesylation and geranylgeranylation of small GTPase signalling proteins. This activity inhibits osteoclast activity and reduces bone resorption and turnover. In postmenopausal women, it reduces the elevated rate of bone turnover, leading to, on average, a net gain in bone mass.

Signs and Symptoms · 1건

There is no experience of acute overdose. Two patients received zoledronate (32 mg) over 5 minutes in clinical trials. Neither patient experienced any clinical or laboratory toxicity. Overdosage may cause clinically significant hypocalcemia, hypophosphatemia, and hypomagnesemia.

Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Drug Induced Liver Injury · 6건

Drug Induced Liver Injury Rank (DILIrank 2.0)

Zoledronic acid

vLess-DILI-concern

0

No match

DOI:10.1016/j.drudis.2016.02.015

Effects During Pregnancy and Lactation◉ Summary of Use during Lactation

안전 데이터

HS 번호
2933399090
risk_code
21/22-36/37/38
hazard_code
Xi
safety_code
24/25-36/37/39

Zoledronic acid is not metabolized _in vivio_.

Zoledronate does not inhibit human P450 enzymes in vitro and does not undergo biotransformation in vivo. Route of Elimination: In 64 patients with cancer and bone metastases, on average (± s.d.) 39 ± 16% of the administered zoledronic acid dose was recovered in the urine within 24 hours, with only trace amounts of drug found in urine post-Day 2. Half Life: 146 hours

FDA Pharmacological Classification · 6건

70HZ18PH24

ZOLEDRONIC ACID ANHYDROUS

Established Pharmacologic Class [EPC] - Bisphosphonate

Chemical Structure [CS] - Diphosphonates

Zoledronic acid anhydrous is a Bisphosphonate.

ZOLEDRONIC ACID

MeSH Pharmacological ClassificationAgents that inhibit BONE RESORPTION and/or favor BONE MINERALIZATION and BONE REGENERATION. They are used to heal BONE FRACTURES and to treat METABOLIC BONE DISEASES such as OSTEOPOROSIS.
Absorption, Distribution and Excretion · 3건

A 4mg intravenous dose reaches a Cmax of 370±78.5ng/mL, with a Tmax of 0.317±0.014h, and an AUC of 788±181ng\*h/mL. A 5mg intravenous dose reaches a Cmax of 471±76.1ng/mL, with a Tmax of 0.368±0.005h, and an AUC of 917±226ng\*h/mL.

Zoledronic acid is 39 ± 16% eliminated in the urine as the unmetabolized parent drug.

Zoledronic acid has a renal clearance of 3.7 ± 2.0 L/h.

Cellular LocationsCytoplasm
Metabolite PathwaysZoledronate Action Pathway

용도 및 제조

Uses · 2건

Use (kg) in USA (2002): 1

For the treatment of hypercalcemia of malignancy. Also for the treatment of patients with multiple myeloma and patients with documented bone metastases from solid tumors, in conjunction with standard antineoplastic therapy. In May of 2007, the drug was approved for treatment of Paget's Disease.

응용 분야 · 2건

개요Zoledronic acid is a white, crystalline powder that is available in vials for reconstitution for IV infusion over at least 15 minutes. It does not undergo metabolic transformation and does not inhibit CYP450 enzymes. Clearance of this agent is dependent on the patient's creatinine clearance, not on dose. Serum creatinine levels should be evaluated before every treatment. Zolendronic acid is contraindicated in patients with severe renal impairment.

용도Zoledronic acid induces apoptosis in osteoclasts by inhibiting enzymes of the mevalonate pathway and preventing the isoprenylation of small GTP-binding proteins such as Ras and Rho.

상·하류 제품 정보

상류 원료

삼염화 인인산2-(1H-Imidazol-1-yl)acetyl chloride이미다졸-1-일-아세트산에틸1H-이미다졸-1-아세테이트물

공급사100 곳

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추가 설명

정의ChEBI: An imidazole compound having a 2,2-bis(phosphono)-2-hydroxyethane-1-yl substituent at the 1-position.