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パミドロン酸

Pamidronic Acid

HCID 4674
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基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
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基本情報

CAS
40391-99-9
標準SMILES
NCCC(O)(P(=O)(O)O)P(=O)(O)O
InChIKey
WRUUGTRCQOWXEG-UHFFFAOYSA-N
分子式
C3H11NO7P2
平均分子量
235.07 g/mol
単同位体質量
235.00107495

概要

Pamidronate is a phosphonoacetic acid.

名称と識別子

優先名称
Pamidronic Acid
IUPAC
(3-amino-1-hydroxy-1-phosphonopropyl)phosphonic acid
現地名
パミドロン酸
英語名
Pamidronic acid
分子式
C3H11NO7P2
分子量
235.07

名称と別名

PAMIDRONIC ACIDpamidronate40391-99-9AmidronateAcide pamidronique(3-amino-1-hydroxy-1-phosphonopropyl)phosphonic acidAcido pamidronicoAcidum pamidronicumRibodroat(3-Amino-1-hydroxypropylidene)bisphosphonic acidDTXSID4023414AHPrBP
名称をさらに表示
3-アミノ-1-ヒドロキシプロピリデンビスホスホン酸1-ヒドロキシ-3-アミノプロピリデンビス(ホスホン酸)1-ヒドロキシ-3-アミノプロパン-1,1-ジイルビスホスホン酸2-アミノエチルヒドロキシメチレンビスホスホン酸(1-ヒドロキシ-3-アミノプロパン-1,1-ジイル)ビスホスホン酸(3-アミノ-1-ヒドロキシプロピリデン)ビス(ホスホン酸)[2-アミノエチル(ヒドロキシ)メチレン]ビスホスホン酸(3-アミノ-1-ヒドロキシプロピリデン)ビスホスホン酸1-ヒドロキシ-3-アミノプロピリデンビスホスホン酸パミドロネート3-アミノ-1-ヒドロキシプロピリデンビス(ホスホン酸)パミドロン酸(1-ヒドロキシ-3-アミノプロピリデン)ビスホスホン酸パミドロナートメシル酸デラビルジン1-ヒドロキシ-3-アミノプロパン-1,1-ジイルビス(ホスホン酸)3-アミノ-1-ヒドロキシ-1,1-プロパンジイルビスホスホン酸(3-アミノ-1-ヒドロキシ-1-ホスホノプロピル)ホスホン酸(3-Amino-1-hydroxypropane-1,1-diyl)bis(phosphonic acid)DLVPanolinRescriptorPamidronicaciIflab-bb F1977-0047Delavirdine mesylate
OYY3447OMC(3-Amino-1-hydroxypropylidene)diphosphonic acidDTXCID003414(3-amino-1-hydroxypropylidene)-1,1-biphosphonateaminopropanehydroxydiphosphonateamino-1-hydroxypropane-1,1-diphosphonateRefChem:57113M05BA03

データベース識別子

CAS
40391-99-9
PubChem CID
4674
DTXSID
DTXSID4023414
ChEMBL
CHEMBL834
ChEBI
CHEBI:7903
UNII
OYY3447OMC
EC Number
254-905-2
Nikkaji
J221.669H

物性

構造計算による物性補完中

XLogP
-6.9
極性表面積
161 Ų
水素結合供与体数
6
水素結合受容体数
8
回転可能結合数
4
重原子数
13
形式電荷
0
複雑度
243

実験および物理化学的性質

Drugs · 2 件

Pharmaceuticals

Pharmaceuticals -> Listed in ZINC15

LogP-4.7
Solubility1.58e+01 g/L
Human DrugsBreast Feeding; Lactation; Milk, Human; Bisphosphonates; Bone Density Conservation Agents; Diphosphonates
Melting Point254-262
Physical DescriptionSolid

物理化学的性質

融点
226 · 226-228°C
沸点
658.7 · 658.7±65.0 °C(Predicted)
比重(密度)
1.998 · 1.998±0.06 g/cm3(Predicted)
貯蔵温度
2 · under inert gas (nitrogen or Argon) at 2–8 °C
溶解性
メタノール（ごくわずか、加熱、超音波処理）、水（わずかに、加熱、超音波処理）
酸解離定数(Pka)
1.44 · 1.44±0.10(Predicted)
外見
個体
色
ライトブラウンからベージュ
安定性
吸湿性

安全と法規制

安全情報は参考情報です。供給元の安全データシート（SDS）、適用法令、専門家による評価に代わるものではありません。

GHS分類

GHS Classification · 4 件

Warning

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 24 reports by companies from 4 notifications to the ECHA C&L Inventory.

危険有害性情報

Hazard Classes and CategoriesAcute Tox. 4 (100%)

毒性情報

TreatmentIf overdosage occurs, symptomatic hypocalcemia could also result; such patients should be treated with short-term intravenous calcium. (L1712)
Health EffectsRare cases of uveitis, iritis, scleritis, and episcleritis have been reported, including one case of scleritis, and one case of uveitis upon separate rechallenges.
Adverse EffectsPamidronate correlates with numerous adverse effects, including hypocalcemia and resulting secondary hyperparathyroidism, acute phase response, musculoskeletal pain, various ocular events, and osteonecrosis of the jaw.
Exposure RoutesParenteral (intravenous). Plasma concentration rises rapidly upon IV administration.
Toxicity Summary · 2 件

A small number of cases describe symptomatic hypocalcemia following pamidronate administration. In each case, however, patients had pre-existing derangements contributing to their symptoms, including renal insufficiency and low vitamin D levels secondary to lifestyle, previous GI surgery, and medication history. Recommendations for the management of pamidronate overdose include appropriate correction of the electrolyte disturbance and pre-treatment supplementation with calcium and Vitamin D.

化学と産業

薬理情報

ATC Code · 3 件

M05BA03

M - Musculo-skeletal system

QM - Musculo-skeletal system

Protein BindingPamidronate is approximately 54% protein bound in serum.
Pharmacodynamics · 1 件

Pamidronic acid is a second generation, nitrogen containing bisphosphonate that inhibits osteoclast mediated bone loss It has a wide therapeutic index and a long duration of action as it can be given every 3-4 weeks for certain indications. Patients should be counselled regarding the risk of elevated blood urea nitrogen, renal tubular necrosis, and nephrotoxicity.

Mechanism of Action · 1 件

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. Disruption of the podosomes causes osteoclasts to detach from bones, preventing bone resorption. Nitrogen containing bisphosphonates such as pamidronate 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. pamidronate also activated caspases 3 and 9 which further contribute to apoptosis.

Biological Half-LifeThe mean elimination half life of pamidronate is 28±7 hours.
Metabolism/Metabolites · 2 件

Pamidronate is not metabolized _in vivo_.

Pamidronate is not metabolized and is exclusively eliminated by renal excretion. Route of Elimination: Pamidronate is not metabolized and is exclusively eliminated by renal excretion. Half Life: The mean ± SD elimination half-life is 28 ± 7 hours

関連反応

21 件
反応記録を作成
HRID 49739 の反応式
HRID 49739反応物としてuspto-grants-2004_03
HRID 74141 の反応式
HRID 74141反応物としてuspto-grants-2014_09
HRID 412673 の反応式
HRID 412673生成物としてuspto-grants-2003_05
HRID 980773 の反応式
HRID 980773反応物としてuspto-grants-1987_01
HRID 980774 の反応式
HRID 980774反応物としてuspto-grants-1987_01
HRID 980775 の反応式
HRID 980775反応物としてuspto-grants-1987_01
HRID 980776 の反応式
HRID 980776反応物としてuspto-grants-1987_01
HRID 980777 の反応式
HRID 980777反応物としてuspto-grants-1987_01
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化合物ノート

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このページの内容基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
その他の操作
ノートを作成反応を作成見積依頼を出す
InChI
InChI=1S/C3H11NO7P2/c4-2-1-3(5,12(6,7)8)13(9,10)11/h5H,1-2,4H2,(H2,6,7,8)(H2,9,10,11)
InChIKey
WRUUGTRCQOWXEG-UHFFFAOYSA-N
SMILES
C(P(=O)(O)O)(P(=O)(O)O)(O)CCN

化学的性質

化学的特性White Solid

The mechanism of action of pamidronate is inhibition of bone resorption. Pamidronate adsorbs to calcium phosphate (hydroxyapatite) crystals in bone and may directly block dissolution of this mineral component of bone. In vitro studies also suggest that inhibition of osteoclast activity contributes to inhibition of bone resorption. Pamidronate also targets farnesyl pyrophosphate (FPP) synthase. Nitrogen-containing bisphosphonates (such as pamidronate, alendronate, risedronate, ibandronate and 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 SymptomsSide effects include an allergic reaction, kidney problems, seizures, low levels of calcium, magnesium, or phosphorus in the blood
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Drug Induced Liver Injury · 5 件

Drug-Induced Liver Injury Severity and Toxicity (DILIst)

pamidronate

DILI Negative

Intravenous

DOI:10.1016/j.drudis.2019.09.022

Effects During Pregnancy and Lactation◉ Summary of Use during Lactation

安全データ

hs_code
9999999999
FDA Pharmacological Classification · 5 件

OYY3447OMC

PAMIDRONIC ACID

Established Pharmacologic Class [EPC] - Bisphosphonate

Chemical Structure [CS] - Diphosphonates

Pamidronic acid is a Bisphosphonate.

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 · 3 件

In patients with a creatinine clearance >90mL/min, a 90mg intravenous dose reached a Cmax of 1.92±1.08µg/mL, with a Tmax of 4h, and an AUC of 10.2±6.95µg\*h/mL. In patients with a creatinine clearance 61-90mL/min, a 90mg intravenous dose reached a Cmax of 1.86±0.50µg/mL, with a Tmax of 4h, and an AUC of 10.7—3.91µg\*h/mL.[A203264 In patients with a creatinine clearance 30-60mL/min, a 90mg intravenous dose reached a Cmax of 1.84±0.58µg/mL, with a Tmax of 4h, and an AUC of 10.1±3.38µg\*h/mL. In patients with a creatinine clearance <30mL/min, a 90mg intravenous dose reached a Cmax of 1.93±0.53µg/mL, with a Tmax of 4h, and an AUC of 34.0±8.37µg\*h/mL.

Pamidronate is exclusively eliminated in the urine. By 120 hours after administration, 46±16% of the dose has been eliminated in the urine.

The mean total clearance of pamidronate is 107±50mL/min and the mean renal clearance is 49±28mL/min.

Cellular LocationsCytoplasm
Metabolite PathwaysPamidronate Action Pathway

用途と製造

Uses · 2 件

Use (kg; approx.) in Germany (2009): >10

Pamidronate is in a class of drugs called bisphosphonates. Pamidronate reduces breakdown of the bones. Pamidronate is used in the treatment of Paget's disease of bone; to reduce high levels of calcium in the blood associated with malignancy (cancer); and to reduce the breakdown of bone due to metastases of breast cancer or multiple myeloma. For the treatment of moderate or severe hypercalcemia associated with malignancy

応用分野

使用anticancer

上流・下流製品情報

上流原料

β-アラニン三塩化りんパミドロン酸ナトリウムActivated carbon,decolor水酸化ナトリウムマンニトール