1
UTEROTONICS
INCREASE THE TONUS OF UTERINE MUSCLES
Usage:
• To trigger and increase of uterine contractions
oxytocin
• To accelerate III. birth-time period
oxytocin and ergot uterotonics
• To stop afterbirth bleeding from atonic uterus
oxytocin and ergot uterotonics
• To stop metrorrhagia
ergot uteronics
Greek OXYS = fast, TICHTEIN = to birth, birth acceleration.
OXYTOCINUM – OXYTOCINE (ČL 2005)
Cyclic nonapeptid produced by posterior lobe of the pituitary gland.
Prepared via synthetic route.
H Cys Tyr Ile Gln Asn Cys Pro Leu Gly NH2
2
ERGOT UTEROTONICS
EXCLUSIVELY ISOLATED ALKALOIDS AND THEIR
DERIVATIVES
Ergometrini maleas – Ergometrin-maleinate (ČL 2005)
• Uterotonic
Ergotamini tartras – Ergotamin-tartrate (ČL 2005)
• Uterotonic
• Component of antimigrenics and sedatives
Methylergometrinium tartaricum – Methylergometrin-tartrate
• Uterotonic
HYDRASTIDIS RHIZOMA – GOLDENSEAL RHIZOME
MP: Hydrastis canadensis –
goldenseal (Ranunculaceae);
perenial plant with creeping
rhizome; North America;
vegetative propagation
Drug: dried rhizomes harvested
from 3.5. year of growth
CC: 2,5-6 % isoquinoline alkaloids,
main is hydrastin, kanadin and
berberin
Usage: Heamostyptic (weaker
effect than ergot alkaloids)
O
O
N-CH3
OMe
OMe
O O
hydrastin
phtalidoisoquinoline type
3
BURSAE PASTORIS HERBA – SHEPERDS PURSE HERB
MP: Capsella bursa pastoris – sheperds
purse (Brassicaceae)
Drug: Dried aerial part
CC: cholin, acetylcholin, tyramin,
histamin
flavonoid diosmin
Usage: folk medicine for treatment of
menstruation disorers and
metrorrhagia
4
ANTIPROTOZOICS
Compounds used for treatment of protozoal diseases
• ANTIAMEBICs
• ANTIMALARICs
ANTIAMEBICs
Emetini dihydrochloridum
pentahydricum (ČL 2005)
Source: Ipecacuanhae radix,
Cephaelis ipecacuanha
(Rubiaceae)
Usage: for treatment of
ameboid dysenteria
(Entameba histolytica)
Emetin prevents its
multiplication
N
OMe
MeO
H H
H
NH
H
OMe
OMe
5
ANTIMALARICs
Malaria – the most wide spread disease of warm climate countries.
Originates from several Plasmodium strains (P. vivax, P. malariae, P.
falciparum, P. ovale)
Two development cycles
• sexual (Anofeles – gamets – sporozoits in saliva – transfer to human)
preerythrocytic stadium – 10-14 days of development in hepatic cells,
type of incubation period
• asexual (human, in erythrocytes – schizonts. After their multiplication
erythrocytes disintegrate and released daughter merozoites infiltrate
plasma, and start fever = clinical form of malaria)
Therapeutic interference into phase taking place in human body
QUININI HYDROCHLORIDUM DIHYDRICUM (ČL 2005)
QUININI SULFAS DIHYDRICUS (ČL 2005)
Source: Chinae cortex from different
Cinchona species – (Rubiaceae),
mainly C. succirubra
Trees native to Andes mountains of
tropical America, today highly
specialized part of tropical
agriculture
Quinine is obtained from bark of
hybrids old 6-9 years; content of
alkaloids up to 17 %, quinine upto
2/3
Protoplasmatic poison – stops
numerous enzymatic procedures,
therefor possesses ability to kill
different infectious agents
N
MeO
COH
H
N
H
H
H
H
OH N
H
H
N
MeO
C
H
6
ANTHELMINTICs
Compounds used to suppress intestinal parasites
Infection by helmints is serious health problem – touching half of
world population
In our country
• tapeworm (Taenia)
• roundworm (Ascaris)
• pinworm (Oxyuris or Enterobius vermicularis)
7
FILICIS MARIS RHIZOMA – COMMON MALE FERN
RHIZOME
MR: Dryopteris filix-mas – Common
Male Fern (Dryopteridaceae),
perennial plant of Europe, Asia, and
America
Drug: in autumn harvested, dried
rhizome with sessile leaf base
CC: Filicin; mixture of phloroglucinol
derivatives (mono- to tetracyclic
compounds); cca 25 % of Et2O
extract of drug
Usage: Taenifugum in combination with
laxatives
FILICIS MARIS RHIZOMA
Content compounds
O
OH OH
C
O
C3
H7
OH
COC3
H7
OH OHOH OH
O
C
O
H7
C3
C
H2
C
H2
filixic acid
8
GRANATI CORTEX – POMEGRANATE CORTEX
MP: Punica granatum – pomegranate
(Punicaceae), low tree cultivated in
tropics and subtropics
Drug: dried bark from stems, branches,
roots
CC: 0,-0,7 % of piperidine alkaloids –
pelletierin, isopelletierin, pseudo-
pelletierin
Usage: Taenifugum in combination with
laxative
Pericarp – does not contain alkaloids,
containing up to 28 % of tannins and
pigments. Astringens.
GRANATI CORTEX
Content compounds
N
H
O
H
pelletierin (R)-forma
9
ARECAE SEMEN – ARECA SEED
MP: Areca catechu – areca palm
(Arecaceae); palm 15 m tall,
cultivated in India, Ceylon, Malaysia;
fruit is a drupe containing seed
Drug: dried seed (after getting from fruit
is boiled in water containing
quicklime, than it is dried)
CC: 0,2-0,5 % of alkaloids (arecolin,
arecaidin (reduced pyridine
derivatives), fat, catechin tannins.
Usage: veterinary anthelmitic
ARECAE SEMEN
Contain compounds
N
R2
COOR1
R1 R2
arekolin CH3 CH3
arekaidin H CH3
guvacin H H
guvakolin CH3 H
10
CHENOPODII ETHEROLEUM – WORMSEED ESSENTIAL
OIL
CC: Chenopodium ambrosioides
subsp. anthelminticum –
wormseed (Chenopodiaceae)
Drug: essential oil obtained by
hydrodistillation of fresh
flowering aerial parts
CC: 60-80 % of ascaridol, p-cymen,
limonen, camphor
Usage: Broad spectral anthelmintic,
narrow therapeutic window
Veterinary usage
O
O
hv
alfa-pinen
alfa-terpinen askaridol
CINAE FLOS – SANTONICA FLOWER
CC: Artemisia cina – santonica
(Asteraceae); semi shrub
from Turkmenistan
Drug: dried not opened
inflorescence harvested in
VII and VIII;
CC: essential oil with santonin,
cineol and further terpenes
Usage: veterinary anthelmintic
(do not kill tapeworm)
O
O
O
santonin
11
INSECTICIDES – PREPARATIONS TO KILL
INSECTS
Occurence in families
• Solanaceae
• Liliaceae (Sabadillae semen, Veratri rhizoma)
• Asteraceae (Pyrethri flos)
• Buxaceae (Buxi folium)
• Apocynaceae
12
VERATRI RHIZOMA – FALSE HELLEBORINE
RHIZOME
CC: Veratrum album – false
helleborine. White perennial plant
of mountains medows of Europe
Drug: in autumn harvested dried
rhizome, longitudinaly cutted, often
peeled from roots
CC: 1-1,5 % of alkaloids with true or
modified steroidal skeleton (C-norD-homosteroids
- veratramin and
jervin). Further more alkamins,
esters, glycosides
Usage: Insecticidum
Ester protoveratrins A and B anti-
hypertensive
SABADILLAE SEMEN – SABADILLA SEED
MR: Schoenocaulon officinale –
Sabadilla (Liliaceae); perenial
plant of Middle America
Drug: dried seeds
CC: 1-5 % of alkaloids, assigned
as „veratrin“; mixture
composed of cevadine and
veratridine (esters of
veracevine with angelic acid
resp. veratric acid at C3
Usage: Insecticide (Acetum
sabadillae)
N
O
OH OH
OH
OH
OH
OH
OR
R = kys. veratrová = veratridin
R = kys. angeliková = cevadin
13
PYRETHRI FLOS – PYRETHRUM DAISY FLOWER
MP: Chrysanthemum cinerariifolium –
pyrethrum daisy (Asteraceae);
perennial plant native in Jadran
area, cultivated in Japan, Brazil,
Kenya, India
Drug: dried inflorescence, harvested
from 2- to 6-year old plants before
full opening
CC: esters of chrysanthemic acid (serie
I) a pyrethric (serie II) – pyrethrin,
jasmolin and cinerin; furthermore
essential oil, resin, triterpenes
Usage: contact insecticide (do not affect
warm-blooded animals, do not form
resistance
R1
H
H
O
O
O
R2
R1
= CH3
R1
= CO2
CH3
R2
= CH-CH3
R2
= CH3
R2
= CH2
CH3
(pyrethrová kyselina) serie I
(chrysanthemová kyselina) serie II
pyrethriny I a II
cineriny I a II
jasmoliny I a II
NICOTINE
Dark smelling liquid obtained by
hyydrodistillation of different
Nicotiana species (Solanaceae)
CC: green lobacco leaves
containing 40 % of saccharides
(starch, pectin, cellulose,
soluble sugars), 15-20 % of
proteins and organic acids and
2-10 % of nikotin and other
related alkaloids
Usage: Contact insecticide
N
N
CH3
H
N
N
CH3
H
nikotin
anabasin
14
ANTIURATICS
COLCHICINUM – COLCHICINE (ČL 2005)
Present in testa and tubers of Colchicum
autumnale – autumn crocus
(Liliaceae)
• Cytotoxic activity known from 40ies
of 20th century. Stops cell division,
do not stop chromosome division,
cuases polyploidia
• Antiuratic ruring acute atacks of
gout – painfull iinflammations of
joints, where are gathered crystals
of uric acid. Stops the movement
and penetration of inflammatory
cells.
• Serie of side effects
O
N
H
MeO
O
OMe
OMe
R2
R1
3
Kolchicin CH3 COCH3
Demekolcin CH3 CH3
3-Desmethylkolchicin H COCH3
R1 R2
15
ANTIPHLOGISTICS – ANTI-INFLAMMATORY
PREPARATIONS
Because of anti-inflammatory, analgesic and antipyretic activities
are natural antiphlogistics often used pharmaceuticals.
Salicis cortex (ČL 2005)
Salviae officinalis folium (ČL 2005)
Hyperici herba (ČL 2005)
Matricariae flos (ČL 2005)
Arnicae flos (ČL 2005)
Balsamum peruvianum (ČL 2005)
Semen aesculi hippocastani
16
SEMEN AESCULI HIPPOCASTANI – HORSE CHESTNU SEED
MR: Aesculus hippocastanum – horse
chestnut (Hippocastanaceae); tree
native at Balcaninan peninsula,
cultivated widely as a ornamental
tree
Drou: fresh or dried seeds
CC: uop to 13 % of saponins, main is
aescin, what is a mixture of
esterified aglycons protoaescigenine
and barringtogenol C;
flavonoid glycosides, starch, fatty
oil, proteins
Testa contains coumarin aesculin
Usage: antiphlogistic and antiexsudative;
venopharmac; varixes, ulcus
cruris
SEMEN AESCULI HIPPOCASTANI
Content compounds
O
COOH
O
OH
O
O
Glc
Glc
CH2
OH
CH2OH
OH
OR2
OR1
OOH
OH
O
protoaescigenin
eskuletin
beta-aescin: R1 = zbytky kys. tiglinové, angelikové, alfa-methylmáselné
R2 = acetyl
17
APHRODISIACs
After development of SILDENAFIL lost biogenic aphrodisiacs partially their
importance
• YOHIMBIN isolated from Yohimbea cortex (Pausinystalia yohimbe – yohimbe
(Rubiaceae). Up to 30 m tall tree native to West Africa, common in Camerun.
Triggers hyperaemia of pelvis minor and stimulates centra in medulla
oblongata driving sacral area
N
H
N
H H
H
OH
COOCH3
yohimbin
18
ROBORANTS - GERIATRICS - TONICs
Group of compounds, which should bring overall enforcing effect,
increase of physical strenght, stimulation of intellectual output.
Used as preparations to delay and to supress symptoms of
eldering or treatmant od diseases connected with age.
Ginseng radix
Eleuterococci radix
Rhodiolae radix
Schizandrae fructus
Vitamins
Lecitins
19
GINSENG RADIX – GINSENG ROOT
CC: Panax ginseng – ginseng
(Araliaceae); Asian mountain
perennial plant with beet-shaped
root, up to 50 cm tall stem, 5membered
leaves. Fruits – red
berries.
Drug: dried whole or cutted root of 5-6
years old plants; different
processing (white and red ginseng)
CC: at least 0,40 % of mixture of
ginsenosides R-G 1
Usage: geriatrics, roborans, adaptogen
GINSENG RADIX
Aglycons of steroidal saponins
OH
OH
H
H
R
OH
R = H 20-S-protopanaxadiol
R = OH 20-S--protopanaxatriol
20
20
ELEUTHEROCOCCI RADIX – SIBERIAN GINSENG ROOT (ČL 2005)
MR: Eleutherococcus senticosus –
siberian radix (Araliaceae); 2,5 m tall
woody plant 5-memebered leaves;
cultivated in Asia
Drug: whole or cutted dried root and
rhizome
CC: saponins – glycosides of oleanolic
acid, assigned as eleuterosides A-M;
furthermore – eleuterany A-G,
lignans, coumarins
Usage: roborans, tonic.
Eleuterans show hypoglycaemic
effect.
SCHIZANDRAE FRUCTUS – FIVE FLAVOR BERRY
MR: Schizandra chinensis –
schizandra (Schizandraceae);
creeping woody plant of
northern China.
Drug: dried fruits
CC: compounds of lignane type (till
present described cca 40) with
dibenzocyclooctadiene sceleton
(schizandrins, gomisins)
Usage: part of geriatric mixtures,
hepatoprotective, stimulant
OH
OMe
MeO
MeO
MeO
MeO
schizandrin
21
CORRIGENTs
Corrigents are compounds without physiological effect. Their
properties can mask unpleasant taste, smell or colour of
medicinal preparations.
Corrigents of taste – sugars, sirups, liquorice extract
Corrigents of odour – chosen essential oils
Corrigents of colour – correction of esthetic image of drug,
decrease of possibility of mischange (anthocyanins, pigments of
fruits, betalains of red beet, chlorophylls, carotenoids)
22
AURANTII AMARI PERICARPIUM – PERICARP OF BITTER ORANGE (ČL 2005)
(Syn.: AURANTII AMARI EPICARPIUM ET MESOCARPIUM)
MP: Citrus aurantium ssp. aurantium; (Citrus
aurantium ssp. amara) – bitter orange tree
(Rutaceae); evergreen tree native in India,
cultivated in Sicilia, Spain, Lybia.
Drug: dried pericarp of matured fruit, peeled of
spongeous white albedo
CC: at least 20 ml essential oil /kg of drug
(limonen, linalol, citral, geraniol, nerol);
flavonoids of bitter taste hesperidin,
neohesperidin; in albedo further bitter
substances; in flavedo β-caroten, lycopen,
xanthophyl;
Usage: Aromatic amare, corrigent, carminative;
liquors manufacturing, beverages
Galenic preparation: Aurantii amari pericarpii
extract
AURANTII AMARI PERICARPIUM – BITTER ORANGE PERICARP (ČL 2005)
CHO
NH2
COOCH3
O
OOH
ORha-Glc
R1
R2
O
O
OMe
MeO
MeO OMe
OMe
limonen
80-90 %
citral
methylester
kys. anthranilové
[6-O] naringin R1 = H R2 = OH
[2-O] hesperidin R1 = OH R2 = OMe
auranetin
23
AURANTII AMARI FLOS – BITTER ORANGE FLOWER (ČL 2005)
MR: Citrus aurantium ssp. aurantium; (Citrus
aurantium ssp. amara) (Rutaceae);
Drug: whole dried not opened flower
CC: at least 8 % of flavonoids expressed as
naringin
Usage: corrigens
PERICARPIUM CITRI – LEMON TREE PERICARP
MP: Citrus limonia – Lemon tree (Rutaceae);
evergreen tree native to India, cultivated
in subtropics
Drug: dried, spiral-shaped peeled external
part of pericarp – flavedo without albedo
CC: 2,5-6 % of essential oil (D-limonen,
citral, low amount citronellal,
geranylacetate), methylester of anthranilic
acid, citropten (5,7-di-methoxycoumarin)
Usage: corrigents, aromatic amare
24
BERGAMOTTAE ETHEROLEUM
– BERGAMOT ESSENTIAL OIL
MP: Citrus aurantium ssp. bergamia
– bergam lemon tree;
evergreen small tree of tropics
and subtropics, fruits with
strong pericarp, not edible
Drug: essential oil obtained by
pressing of fresh pericarp
CC: contains at least 30,0 % of
esters expressed as linalylacetate,
limonen,
linalol);bergapten (5-
methoxyfuranocoumarin)
Usage: corrigens of odour;
cosmetics, Earl Grey
OCOCH3 OH
OO O
OMe
linalylacetát limonen linalol
bergapten
IRIDIS RHIZOMA – IRIS RHIZOME
MR: Iris germanica, I. pallida, I. florentina;
perennial plants native in Mediterranean;
produced in Italy, France, Morocco
Drug:dried rhizomes of three year old plants,
without roots and leaves, sun dried, typical
smell
CC: 0,1-0,2 % of essential oil (10 % of irons),
aromatic unsatturated ketons; starch,
mucilage
Usage: corrigens of odour and taste, aromatic
mucilaginose, parfumes
O
beta-iron
25
VANILLAE FRUCTUS – VANILLA FRUIT
MP: Vanilla planifolia – vanilla orchid, V. tahitensis
(Orchidaceae); perrenial climbing, dioecious
epifytes, cultivated in tropics (temperature do
not fall bellow 18 0C, high humidity);
prepagation vegetative, in cultures necessary
arteficial pollination (native by hummingbirds)
Drug: dried fermented fruits (purse)
CC: Fragrant compounds in papillas on the inner
side of pericarp; vanilin is formed during
fermentation from vaniloside via action of
oxidases and hydrolases. Tahitian vanilla
contains also anisalcohol and anisaldehyde
Usage: Aromatic corrigent of taste and odour
VANILLAE FRUCTUS
CH2
OH
O-Glc
OMe
CH2
OH
OH
OMe
OH
OMe
CHO
O-Glc
OMe
CHO
vanilolosid
hydrolysa
vanilylalkohol
oxidace
vanilin
hydrolysa
vanilosid
26
ROSAE ETHEROLEUM – ROSE ESSENTIAL OIL
MP: Rosa centifolia – rose, R. damas cena, R.
gallica and other ssp. (Rosaceae)
Drug: fresh corona leaves, processed by
hydrodistillation to obtain essential oil (1
kg of essential oil = 4000 kg of raw
material)
CC: essential oil composed of acyclic
oxygenated terpenes (geraniol, nerol,
citronellol, fenylethylalcohol)
Usage: corrigens of odour
Substitute: Geranii etheroleum - Pelargonium
sp. (Geraniaceae). Contains 65 % of
terpenic alcohols alkoholů (as geraniol).